Triethylamine → [5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonylamine]-acetic acid methyl ester

HRID 1819941Notes

Reaction equation

HRID 1819941 reaction equation
[C:1]([Si:5]([CH3:37])([CH3:36])[O:6][CH:7]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[S:25][C:24]([S:26](Cl)(=[O:28])=[O:27])=[C:23]([CH3:30])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:31])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:39][O:40][C:41](=[O:44])[CH2:42][NH2:43].CCN(CC)CC>ClCCl>[CH3:39][O:40][C:41](=[O:44])[CH3:42].[C:1]([Si:5]([CH3:37])([CH3:36])[O:6][CH:7]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[S:25][C:24]([S:26]([NH2:43])(=[O:28])=[O:27])=[C:23]([CH3:30])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 578900895-(1-{4-[2-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonyl chloride

Product 1

HCID 68625648[5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonylamine]-acetic acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aliquot of 5-(1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonyl chloride (step D) (4 ml, 1.5 mmol) is added to a suspension of glycine methyl ester hydrochloride (565 mg, 4.5 mmol) and Et3N (0.94 ml, 6.75 mmol) in dichloromethane (10 ml) at 0° C. It is stirred at RT overnight, concentrated, and partitioned between EtOAc and 1N HCl. The organic layer is concentrated and chromatographed (Hex to 20% EtOAc/Hex) to give the title product (380 mg, 40%).

Workup

  1. concentrationconcentrated
  2. custompartitioned between EtOAc and 1N HCl
  3. concentrationThe organic layer is concentrated
  4. customchromatographed (Hex to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-b0aec8f338c44af6b74f65601edace89
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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