Chloromethyl chloroformate → HCID 23387518, compound

HRID 489016Notes

Reaction equation

HRID 489016 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][OH:21])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl[C:23]([O:25][CH2:26][Cl:27])=[O:24]>C(Cl)Cl.N1C=CC=CC=1>[C:23](=[O:24])([O:25][CH2:26][Cl:27])[O:21][CH2:20][CH2:19][O:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 2

HCID 62754Chloromethyl chloroformateHCID 23387517HCID 23387517, compound

Product 1

HCID 23387518HCID 23387518, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(N-CBz-L-valyloxy)-ethanol (12. 0 g, 40.6 mmol) and pyridine (19.7 mL, 0.24 mmol) in CH2Cl2 (300 mL) at 0° C., was added dropwise chloromethyl chloroformate (10.5 g, 81.2 mmol). After 30 min at 0° C., the reaction mixture was washed with H2O (200 mL). The H2O phase was washed with CH2Cl2 (100 mL) and the solvent of the combined organic phases was removed under reduced pressure. The crude product was column chromatographed (silica gel, 0.5→1% MeOH in CH2Cl2), to give 8.26 g 2-(N-CBz-L-valyloxy)-ethyl chloromethyl carbonate.

Workup

  1. washthe reaction mixture was washed with H2O (200 mL)
  2. washThe H2O phase was washed with CH2Cl2 (100 mL)
  3. customthe solvent of the combined organic phases was removed under reduced pressure
  4. customchromatographed (silica gel, 0.5→1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c51a70d02d324e3b94bcffaa4708f2f9
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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