Methyl chloroformate → HCID 58975161, compound

HRID 737041Notes

Reaction equation

HRID 737041 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH:6]1[CH2:9][CH:8]([NH:10][C:11](=[O:36])[C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:22]3)(=[O:20])=[O:19])=[CH:14][CH:13]=2)[CH2:7]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:5][O:4][C:2]([N:6]1[CH2:9][CH:8]([NH:10][C:11](=[O:36])[C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:22]3)(=[O:19])=[O:20])=[CH:14][CH:13]=2)[CH2:7]1)=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 58975099HCID 58975099, compound

Product 1

HCID 58975161HCID 58975161, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl chloroformate (60 μL, 73 mg, 0.78 mmol, 3.1 equiv) to a suspension of N-azetidin-3-yl-4-(3-phenyl-indole-1-sulfonyl)-benzamide (108 mg, 0.250 mmol, 1 equiv) and triethylamine (140 μL, 100 mg, 1.0 mmol, 4.0 equiv) in anhydr (CH2Cl2 (3 mL). Observe a vigorous gas evolution. After stirring 4 h, rotary evaporate the reaction solution. Transfer the resultant material to a column of silica gel (80 mm×20 mm dia.) and elute (20-60% EtOAc/hex) to yield 84 mg (69%) of 3-[4-(3-phenyl-indole-1-sulfonyl)-benzoylamino]-azetidine-1-carboxylic acid methyl ester as an off-white foam. MS (m/e): 489.96 (M+1); 488.09 (M−1).

Workup

  1. customrotary evaporate the reaction solution
  2. washelute (20-60% EtOAc/hex)

Sources & evidence

ORD record
ord-70eb99ef80c24fac8339abb4f75530d4
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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