Ethyl 2-oxodecanoate → 5-t-butoxycarbonylmethyl-3-(1-ethoxycarbonylnonylamino)-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719134Notes

Reaction equation

HRID 1719134 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][CH:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O=[C:29]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[C:14]([O:13][C:11]([CH2:10][N:7]1[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][CH:3]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:2]([NH:1][CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:8]1=[O:9])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 12750087Ethyl 2-oxodecanoateHCID 135331903-amino-5-t-butoxycarbonylmethyl-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 202675575-t-butoxycarbonylmethyl-3-(1-ethoxycarbonylnonylamino)-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 78%

Procedure

1.1 g of the compound obtained in Example 20 was reacted with 3.0 g of ethyl 2-ketodecanoate in the same manner as described in Example 21. The reaction product was fractionated and purified by silica gel column chromatography using a 9:1 mixture of benzene and ethyl acetate as the eluent. Thus, there was obtained 1.3 g of the desired compound in the form of an oily material.

Workup

  1. custompurified by silica gel column chromatography
  2. additiona 9:1 mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-681f1b88cabf49d1b7e5bfe5d4a24321
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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