Dicyclohexylcarbodiimide → HCID 178445958, compound

HRID 1279187Notes

Reaction equation

HRID 1279187 reaction equation
[N:1]1(C(OC(C)(C)C)=O)CCC[C@H]1C(O)=O.[NH:16]1[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C:22]([NH:24][C@H:25]([C:32]([NH:34][C@H:35]([C:46]([NH:48][C@H:49]([C:52]([NH:54][C@H:55]([C:64]([NH:66][C@@H:67]([C:78]([NH:80][C@H:81]([C:86]([NH:88][C@H:89]([C:97]([N:99]1[CH2:110][CH2:109][CH2:108][C@H:100]1[C:101]([NH:103][CH2:104][C:105]([OH:107])=O)=[O:102])=[O:98])[CH2:90][CH2:91][CH2:92][NH:93][C:94](=[NH:96])[NH2:95])=[O:87])[CH2:82][CH:83]([CH3:85])[CH3:84])=[O:79])[CH2:68][C:69]1C2C(=CC=CC=2)NC=1)=[O:65])[CH2:56][C:57]1[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=1)=[O:53])[CH2:50][OH:51])=[O:47])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)=[O:33])[CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1)=[O:23].C1CCC(N=[C:118]=[N:119][CH:120]2[CH2:125][CH2:124][CH2:123][CH2:122][CH2:121]2)CC1>C(Cl)Cl>[NH:16]1[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C:22]([NH:24][C@H:25]([C:32]([NH:34][C@H:35]([C:46]([NH:48][C@H:49]([C:52]([NH:54][C@H:55]([C:64]([NH:66][C@@H:67]([C:78]([NH:80][C@H:81]([C:86]([NH:88][C@H:89]([C:97]([N:99]1[CH2:110][CH2:109][CH2:108][C@H:100]1[C:101]([NH:103][CH2:104][C:105]([NH2:1])=[O:107])=[O:102])=[O:98])[CH2:90][CH2:91][CH2:92][NH:93][C:94](=[NH:96])[NH2:95])=[O:87])[CH2:82][CH:83]([CH3:85])[CH3:84])=[O:79])[CH2:68][C:69]1[C:121]2[C:120](=[CH:125][CH:124]=[CH:123][CH:122]=2)[NH:119][CH:118]=1)=[O:65])[CH2:56][C:57]1[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=1)=[O:53])[CH2:50][OH:51])=[O:47])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)=[O:33])[CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1)=[O:23]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 178445959HCID 178445959, compound

Product 1

HCID 178445958HCID 178445958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, the obtained Boc-Gly-MBHA resin was washed with 8 mL of DCM (4 times, 1 minute each) and then it was filtered. After that the product was treated with stirring in turn with 8 mL of DCM solution containing 60% TFA (20 minutes), 4 mL of DCM (3 times, 15 seconds each), 3 mL of DMF solution containing 1 mL of DIEA (twice, 1 minute each), and 8 mL of DMF (6 times, 40 seconds each) under argon stream. In addition, filtration was performed at each treatment. Next, 2 mmole of Boc-Pro-OH corresponding to the ninth amino acid residue of the amino acid sequence of pGlu-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-dissolved in 4 mL of DCM. DCC (0.5M-DCM solution) 1.5 mL was added to the solution in an amino acid activation container, then the solution was allowed to react for 7 minutes. After that, the reaction mixture was filtered and transferred to a concentration container. Then 3 mL of DMF was added to the reaction mixture, and the DCM was distilled off under argon stream. Next the residue to which 3 mL of DMF was added was transferred to said reaction vessel for peptide solid phase synthesis, then allowed to react for 30 minutes. Subsequently the product was washed with 8 mL of DCM (6 times, 20 seconds each), then filtered, thereby obtaining Boc-Pro-Gly-MBHA resin.

Workup

  1. washSubsequently, the obtained Boc-Gly-MBHA resin was washed with 8 mL of DCM (4 times, 1 minute each) and then it
  2. filtrationwas filtered
  3. additionAfter that the product was treated
  4. additioncontaining 60% TFA (20 minutes), 4 mL of DCM (3 times, 15 seconds each), 3 mL of DMF solution
  5. additioncontaining 1 mL of DIEA (twice, 1 minute each), and 8 mL of DMF (6 times, 40 seconds each) under argon stream
  6. filtrationIn addition, filtration
  7. customto react for 7 minutes
  8. filtrationAfter that, the reaction mixture was filtered
  9. additionThen 3 mL of DMF was added to the reaction mixture
  10. distillationthe DCM was distilled off under argon stream
  11. additionNext the residue to which 3 mL of DMF was added
  12. customreaction vessel
  13. customto react for 30 minutes
  14. washSubsequently the product was washed with 8 mL of DCM (6 times, 20 seconds each),
  15. filtrationthen filtered

Sources & evidence

ORD record
ord-8b7b043590504c6598155f54663f6cb6
Source dataset
uspto-grants-2002_09
Patent number
US06448031B1

Reaction notes

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