Pyridine → HCID 23387473, compound

HRID 488991Notes

Reaction equation

HRID 488991 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[C:7]([O:11][C:12]([NH:14][C@H:15]([C:19]([O:21][CH2:22][CH:23]([CH2:25][O:26][C:27](=[O:40])[C@H:28]([CH:37]([CH3:39])[CH3:38])[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[OH:24])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].N1C=CC=CC=1>C(Cl)Cl>[Cl:6][CH2:5][O:4][C:2]([O:24][CH:23]([CH2:25][O:26][C:27](=[O:40])[C@H:28]([CH:37]([CH3:39])[CH3:38])[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:22][O:21][C:19](=[O:20])[C@H:15]([CH:16]([CH3:18])[CH3:17])[NH:14][C:12]([O:11][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:13])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 23387479HCID 23387479, compound

Product 1

HCID 23387473HCID 23387473, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloromethyl chloroformate (2.70 mL, 30 mmol) was added to a solution of 1,3-di-O-(N-tert-butoxycarbonyl-L-valyl)glycerol (7.27 g, 14.8 mmol) and pyridine (7.2 mL, 89 mmol) in 60 mL dry CH2Cl2, in an ice bath, under N2. After stirring for 1 h 45 min, the reaction mixture was diluted with 100 mL CH2Cl2 and washed with 40 mL water. The aqueous phase was reextracted with 20 mL H2O. The organic phases were combined, washed with 40 mL saturated NaHCO3, followed by 2×50 mL brine, dried over Na2SO4, and concentrated under vacuum. Flash column chromatography on silica gel with 2/1 hexane-EtOAc gave 8.03 g (93%) of the title compound (alternative nomenclature: 1,3-bis(N-tert-butoxycarbonyl-L-valyloxy)-2-propyl chloromethyl carbonate).

Workup

  1. washwashed with 40 mL water
  2. washwashed with 40 mL saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e72e1dc00a8f4edea1c7efdb6f609661
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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