Methyl chloroformate → 5-[(Tert-butoxycarbonylmethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

HRID 1185662Notes

Reaction equation

HRID 1185662 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH3:6][CH2:7][O:8][C:9]([CH:11]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:12]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:10].CN1CCOCC1>ClCCl>[CH3:6][CH2:7][O:8][C:9]([CH:11]1[CH2:15][CH2:14][CH:13]([CH2:16][N:17]([CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C:2]([O:4][CH3:5])=[O:3])[N:12]1[C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])=[O:10]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 666209305-[(Tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 666203185-[(Tert-butoxycarbonylmethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl esterYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloroformate (0.065 mL, 0.85 mmol) was added to a solution of 5-[(tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (300 mg, 0.77 mmol) and 4-methylmorpholine (0.12 mL, 1.2 mmol) in dichloromethane (10 mL) at 0° C. After 15 minutes the mixture was diluted with dichloromethane (30 mL) and washed with water (15 mL), saturated ammonium chloride (15 mL) and saturated sodium chloride (15 mL). The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure to provide 5-[(tert-butoxycarbonylmethyl-methoxycarbonyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (304 mg, 0.68 mmol, 88%). C21H36N2O8 calculated 444.3, observed [M+1]+445.3; rt=2.58 min.

Workup

  1. washwashed with water (15 mL), saturated ammonium chloride (15 mL) and saturated sodium chloride (15 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fa9e0a1158234f7fb98ddc6d44210e8e
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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