Chloroform → HCID 13419961, compound

HRID 1262888Notes

Reaction equation

HRID 1262888 reaction equation
C(N(CC)CC)C.C(Cl)(Cl)Cl.[C:12]([O:16][C:17]([NH:19][C@H:20]([C:33](O)=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:24][CH:23]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].N#N.Cl.[CH3:39][NH:40][C@@H:41]([C:46]([NH:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:47])[CH2:42][CH2:43][S:44][CH3:45]>O1CCCC1>[NH:19]([C:17]([O:16][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:18])[C@H:20]([C:33]([N:40]([CH3:39])[C@@H:41]([C:46]([NH:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[O:47])[CH2:42][CH2:43][S:44][CH3:45])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 7017901Boc-Tyr(tBu)-OHHCID 86739483HCID 86739483, compound

Product 1

HCID 13419961HCID 13419961, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method of part A of Example 5 and using triethylamine instead of diisopropylethylamine and chloroform as a cosolvent with tetrahydrofuran, N-(tert-butyloxycarbonyl)-O-(tert-butyl)-L-tyrosine (2.13 g.) was condensed with N2 -methyl-N-(3-phenylpropyl)-D-methioninamide hydrochloride (2.0 g.). The product, [N-(tert-butyloxycarbonyl)-O-(tert-butyl-L-tyrosyl]-N2 -methyl-N-(3-phenylpropyl)-D-methioninamide, was purified by crystallization, the first crop (1.51 g., m.r. 129°-130° C.) from ethyl acetate, the second crop (0.53 g.) from ethyl acetate-hexane.

Workup

  1. customThe product, [N-(tert-butyloxycarbonyl)-O-(tert-butyl-L-tyrosyl]-N2 -methyl-N-(3-phenylpropyl)-D-methioninamide, was purified by crystallization
  2. customthe first crop (1.51 g., m.r. 129°-130° C.)

Sources & evidence

ORD record
ord-432234bf99df459a9f293f4f16b0315c
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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