Methanol → HCID 131710736, compound

HRID 2397833Notes

Reaction equation

HRID 2397833 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])=[O:7])(C)(C)C.C(O[C:20]([NH:22][C@H:23](C(O)=O)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)=[O:21])(C)(C)C.C(O[C:47]([NH:49][C@H:50](C(O)=O)[CH2:51][S:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:48])(C)(C)C.[CH:63]1([C:69](O)=O)[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]1.[CH3:72][OH:73]>C(N(CC)CC)C>[CH3:72][O:73][C:12](=[O:14])[C@H:9]([CH2:10][O:11][CH2:69][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[NH:8][C:6](=[O:7])[C@H:23]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:29][CH:30]=1)[NH:22][C:20](=[O:21])[C@H:50]([CH2:51][S:52][CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[NH:49][C:47]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:48]

Participants

7

Reactant 5

HCID 887MethanolHCID 7413Cyclohexanecarboxylic acidHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 2724757L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-S-(phenylmethyl)-

Product 1

HCID 131710736HCID 131710736, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Nα-Cyclohexylcarbonyl-S-benzyl-L-cysteinyl-O-benzyl-L-tyrosyl-O-benzyl-L-serine methyl ester is obtained by reacting Nα-t-butoxycarbonyl-L-serine resin (10 g.) successively with 11.2 g., 30 mmol of Nα-t-butoxycarbonyl-O-benzyl-L-tyrosine, 9.4 g., 30 mmol, of Nα-t-butoxycarbonyl-S-benzyl-L-cysteine and 3.9 g., 30 mmol, of cyclohexane carboxylic acid in the solid phase procedure according to Example 10. The resin is suspended in 250 ml. of absolute methanol containing 25 ml. of triethylamine at room temperature for twenty hours. The resin is removed by filtration. Evaporation of the filtrate gives the crude ester which is purified by chromatography over silica gel in ethyl acetate. The appropriate fractions are chosen by thin layer chromatography, evaporated, and the product held at high vacuum to remove solvents; 3.4 g., [α]D23 -25° (c 1.01, methanol).

Workup

  1. customThe resin is removed by filtration
  2. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-1c7fb65b3786416ea74ede5b597a9f43
Source dataset
uspto-grants-1977_05
Patent number
US04022759

Reaction notes

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