Dimethylformamide dimethyl acetal → HCID 9858173, compound

HRID 858964Notes

Reaction equation

HRID 858964 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][C:16]([CH3:21])([N+:18]([O-:20])=[O:19])[CH3:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22]OC(OC)N(C)C>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][C:16]([CH3:21])([N+:18]([O-:20])=[O:19])[CH3:17])[C:10]([O:12][CH3:22])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 9836076HCID 9836076, compound

Product 1

HCID 9858173HCID 9858173, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-t-Butoxycarbonylamino-6-methyl-6-nitroheptanoic acid (3.90 g, 12.81 mmol) was dissolved in dichloromethane (20 ml) and dimethylformamide dimethylacetal (2.6 ml, 19.22 mmol) was added. The mixture was stirred at room temperature for 20 h. Dimethylformamide dimethylacetal (1.74 ml, 12.8 mmol) was added and the mixture was stirred for 4 h. The mixture was washed with 0.5N hydrochloric acid (30 ml), saturated aqueous sodium hydrogencarbonate solution (30 ml) and saturated brine (30 ml). The solvent was evaporated by concentration under reduced pressure to give the objective compound (2.53 g, yield 62%).

Workup

  1. stirringthe mixture was stirred for 4 h
  2. washThe mixture was washed with 0.5N hydrochloric acid (30 ml), saturated aqueous sodium hydrogencarbonate solution (30 ml) and saturated brine (30 ml)
  3. customThe solvent was evaporated by concentration under reduced pressure

Sources & evidence

ORD record
ord-84b38c29497745069ba21508a02ab12f
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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