Dimethylcarbamoyl Chloride → Dimethyl-carbamic acid 1-[4-(3-phenyl-indole-1-sulfonyl)-benzoyl]-azetidin-3-yl ester

HRID 737036Notes

Reaction equation

HRID 737036 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:18]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[O:7])[CH2:3]1.C(N(CC)CC)C.[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>CN(C)C1C=CN=CC=1.ClCCl>[C:26]1([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]([S:14]([C:11]3[CH:10]=[CH:9][C:8]([C:6]([N:4]4[CH2:5][CH:2]([O:1][C:41](=[O:42])[N:40]([CH3:44])[CH3:39])[CH2:3]4)=[O:7])=[CH:13][CH:12]=3)(=[O:16])=[O:15])[CH:18]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 58975046(3-Hydroxy-azetidin-1-yl)-[4-(3-phenyl-indole-1-sulfonyl)-phenyl]-methanone

Product 1

HCID 58975154Dimethyl-carbamic acid 1-[4-(3-phenyl-indole-1-sulfonyl)-benzoyl]-azetidin-3-yl esterYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine (3-Hydroxy-azetidin-1-yl)-[4-(3-phenyl-indole-1-sulfonyl)-phenyl]-methanone (95 mg, 0.219 mmol), triethylamine (0.200 mL, 1.43 mmol, excess) and 4-dimethylaminopyridine (5 mg, 0.04 mmol) in dichloromethane (1.0 mL) and treat with N,N-dimethylcarbamoyl chloride (0.050 mL) at room temperature. Stir for 15 h, load directly onto pre-packed silica gel column and purify by flash column chromatography (EtOAc/Hexanes) to yield 82 mg of Dimethyl-carbamic acid 1-[4-(3-phenyl-indole-1-sulfonyl)-benzoyl]-azetidin-3-yl ester as a white foam (74%). LRMS: MH+ 503.97.

Workup

  1. customload directly onto pre-packed silica gel column and purify by flash column chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-87716b4d151d4c09a088177a297a7c42
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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