Trifluoroacetic acid → HCID 53706041, compound

HRID 371803Notes

Reaction equation

HRID 371803 reaction equation
[CH3:1][O:2][C:3](=[O:41])[C@H:4]([CH2:37][CH:38]([CH3:40])[CH3:39])[NH:5][C:6](=[O:36])[C@@H:7]([CH3:35])[NH:8][C:9](=[O:34])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)[NH:11]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.[C:49]([O:53][C:54]([NH:56][C@H:57]([C:67]([OH:69])=O)[CH2:58][O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:55])([CH3:52])([CH3:51])[CH3:50].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C.ClCCl>[CH3:1][O:2][C:3](=[O:41])[C@H:4]([CH2:37][CH:38]([CH3:40])[CH3:39])[NH:5][C:6](=[O:36])[C@@H:7]([CH3:35])[NH:8][C:9](=[O:34])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)[NH:11][C:67](=[O:69])[C@H:57]([CH2:58][O:59][CH2:60][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)[NH:56][C:54]([O:53][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:55]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 53689027HCID 53689027, compound

Product 1

HCID 53706041HCID 53706041, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Nα -t-Butoxycarbonyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanyl-L-leucine methyl ester is prepared by deprotecting 11.4 g. (20 mmol) of Nα -t-butoxycarbonyl-O-benzyl-L-tyrosyl-D-alanyl-L-leucine methyl ester with 50 ml. of trifluoroacetic acid in 40 ml. of dichloromethane at 20° C. for 12 minutes. The mixture is evaporated to dryness at 40° C. under reduced pressure and the residue twice taken into dichloromethane and evaporated to dryness followed by drying under high vacuum for 2 hours. The oily product is dissolved in 70 ml. of dimethylformamide and treated at 10° C. with 10 ml. of triethylamine so that a pH of 7 is obtained. Additional triethylamine, 2.8 ml. (20 mmol) is added, followed by 6 g. (20 mmol) of Nα -t-butoxycarbonyl-O-benzyl-L-serine, 2.7 g (20 mmol) of 1-hydroxybenztriazole and (at -5° C.) 4.4. g. of dicyclohexylcarbodiimide. The mixture is slowly stirred to room temperature for two days. The mixture is filtered and the filtrate evaporated at 50° C. under reduced pressure. The residue is dissolved in dichloromethane and filtered. The solution is evaporated to yield an oil which crystallizes from dichloromethane and ether; 10.7 g.; m.p. 67°-71° C.

Workup

  1. customThe mixture is evaporated to dryness at 40° C. under reduced pressure
  2. customevaporated to dryness
  3. customby drying under high vacuum for 2 hours
  4. dissolutionThe oily product is dissolved in 70 ml
  5. additionof dimethylformamide and treated at 10° C. with 10 ml
  6. customof triethylamine so that a pH of 7 is obtained
  7. addition(20 mmol) is added
  8. filtrationThe mixture is filtered
  9. customthe filtrate evaporated at 50° C. under reduced pressure
  10. dissolutionThe residue is dissolved in dichloromethane
  11. filtrationfiltered
  12. customThe solution is evaporated
  13. customto yield an oil which
  14. customcrystallizes from dichloromethane and ether

Sources & evidence

ORD record
ord-33d34e11ff73427a88ae12c41ec8281e
Source dataset
uspto-grants-1978_05
Patent number
US04087418

Reaction notes

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