Cyclopropanecarbonyl chloride → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

HRID 446980Notes

Reaction equation

HRID 446980 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][NH:8][CH:7]2[CH2:10][CH2:11][N:12]([C:13](=[O:29])[CH:14]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:6]12)=[O:4].[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8]([C:33]([CH:30]2[CH2:32][CH2:31]2)=[O:34])[CH:7]2[CH2:10][CH2:11][N:12]([C:13](=[O:29])[CH:14]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:6]12)=[O:4]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 672807484-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 672823014-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 27 (500 mg, 1.22 mmol) in DCM (10 mL) was cooled to 0° C. and treated with TEA (0.26 mL, 1.83 mmol) and cyclopropanecarbonyl chloride (0.13 mL, 1.46 mmol). After 2 h, the reaction mixture was diluted with DCM, washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 44 (580 mg) as a pale yellow-colored foam that was used without further purification. Mass spectrum, m/z [478.6] (M+H)+.

Workup

  1. washwashed successively with 1M HCl, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9607fb9ca73d467ea7d81e9a1b6be7c6
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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