Trifluoroacetic acid → HCID 54535466, compound

HRID 437693Notes

Reaction equation

HRID 437693 reaction equation
[CH3:1][O:2][C:3](=[O:63])[C@@H:4]([CH2:59][CH:60]([CH3:62])[CH3:61])[NH:5][C:6](=[O:58])[C@H:7]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:46][CH:45]=1)[NH:8][C:9](=[O:42])[C@H:10]([CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[NH:11][C:12](=[O:32])[C@H:13]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:14][C:15]([O:17]C(C)(C)C)=O.FC(F)(F)C(O)=O.[CH:71]1(C(O)=O)[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:63])[C@@H:4]([CH2:59][CH:60]([CH3:62])[CH3:61])[NH:5][C:6](=[O:58])[C@H:7]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:46][CH:45]=1)[NH:8][C:9](=[O:42])[C@H:10]([CH2:33][O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[NH:11][C:12](=[O:32])[C@H:13]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:14][C:15]([CH:71]1[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]1)=[O:17]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7413Cyclohexanecarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 53705002HCID 53705002, compound

Product 1

HCID 54535466HCID 54535466, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Nα-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-leucine methyl ester (Example 17), 1 g., 1.16 mmol, is reacted according to the appropriate part of Example 1 with 20 ml. of trifluoroacetic acid, neutralized with triethylamine and coupled with 150 mg., 1.17 mmol, of cyclohexane carboxylic acid using 180 mg., 1.17 mmol, of 1-hydroxybenzotriazole and 240 mg., 1.17 mmol, of dicyclohexylcarbodiimide. The solution is evaporated and the residue triturated with ether. The product is precipitated from isopropanol on cooling as a cream solid; 1 g.; m.p. 158°-160° C.

Workup

  1. custom, 1.16 mmol, is reacted
  2. customThe solution is evaporated
  3. customthe residue triturated with ether
  4. customThe product is precipitated from isopropanol
  5. temperatureon cooling as a cream solid

Sources & evidence

ORD record
ord-ba075f32a378423099c1ba659c0413cb
Source dataset
uspto-grants-1977_06
Patent number
US04031069

Reaction notes

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