Methyl isothiocyanate → 2-Hydroxy-5-methyl-3-[[6-[[(methylamino) thioxomethyl]amino]-2-[[3-(1-naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]amino]-1-oxohexyl]amino]hexanoicacid, 1-methylethyl ester

HRID 846463Notes

Reaction equation

HRID 846463 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH:23][C:24](=[O:48])[CH:25]([CH2:37][C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1)[CH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)[C:7]([NH:9][CH:10]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH:11]([OH:18])[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[O:8].[CH3:49][N:50]=[C:51]=[S:52]>C(Cl)(Cl)Cl>[OH:18][CH:11]([CH:10]([NH:9][C:7](=[O:8])[CH:6]([NH:23][C:24](=[O:48])[CH:25]([CH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)[CH2:37][C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1)[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:51]([NH:50][CH3:49])=[S:52])[CH2:19][CH:20]([CH3:22])[CH3:21])[C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[O:13]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 764955873-[[6-Amino-2-[[3-(1-naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]amino]-1-oxohexyl]amino]-2-hydroxy-5-methylhexanoic acid, 1-methylethyl ester

Product 1

HCID 764881852-Hydroxy-5-methyl-3-[[6-[[(methylamino) thioxomethyl]amino]-2-[[3-(1-naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]amino]-1-oxohexyl]amino]hexanoicacid, 1-methylethyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[2R-[2R*,3S*(S*)]]-3-[[6-amino-2-[[3-(1-naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]amino]-1-oxohexyl]amino]-2-hydroxy-5-methylhexanoic acid, 1-methylethyl ester (Example K), 3.44 g (5.3 mmol), is dissolved in 65 ml of chloroform, 0.42 g (5.7 mmol) of methyl isothiocyanate is added, and the reaction mixture is stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture is concentrated and 2.05 g (53% yield) of the title compound is obtained after flash chromatography over silica gel 60 (230-400 mesh) and elution with hexane-ethyl acetate (1:4); mp softens at 89° C., melts at 93°-95° C.

Workup

  1. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-d05e5184e97a43aabd79d4a476b7b6fd
Source dataset
uspto-grants-1992_08
Patent number
US05135914

Reaction notes

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