Methanol → HCID 71726823, compound

HRID 1664227Notes

Reaction equation

HRID 1664227 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]=[CH2:22])[CH:15]=1)[C@H:9]([OH:12])[CH2:10]Cl)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>C1COCC1.[Cl-].[NH4+]>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C@H:9]1[CH2:10][O:12]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]=[CH2:22])[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67375410HCID 67375410, compound

Product 1

HCID 71726823HCID 71726823, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 3.20 g (10.5 mmol) of [(1S,2S)-1-(3-allyl-benzyl)-3-chloro-2-hydroxy-propyl]-carbamic acid tert-butyl ester in a mixture of 19 ml of THF, 19 ml of MeOH and 21 ml (21 mmol, 2 eq) of 1 N aq sodium hydroxide is stirred at rt for 3 h. The reaction mixture is diluted with 80 ml of saturated aq ammonium chloride solution and extracted with DCM. The organic layer is dried over sodium sulfate and evaporated to give the product.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customevaporated
  4. customto give the product

Sources & evidence

ORD record
ord-ca1b8ab2077b42e38080cf9e6c4b3cd5
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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