Water → HCID 13967208, compound

HRID 381518Notes

Reaction equation

HRID 381518 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([OH:15])[CH2:11]C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]([O-:19])([O-])=[O:17].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[CH2:22]([O:19][C:16](=[O:17])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:10]([OH:15])[CH3:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13037152Boc-4-amino-3-hydroxybutanoic acid

Product 1

HCID 13967208HCID 13967208, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid (2.0 g) in dry DMF (30 ml) at room temperature was added K2CO3 (2.8 g). After 15 min. benzyl bromide (1.7 g) was added. After 16 h the mixture was poured into 200 ml of water and extracted into EtOAc (200 ml×2). The combined organics were washed with 1N NaOH (40 ml); water (40 ml×2); brine (40 ml); dried over MgSO4; filtered, and concentrated under reduced pressure to give an oil. Purification by Flash 40 chromatography using a silica gel column and eluting with 30% EtOAc/hexane gave 2.1 g of the title compound as a colorless oil. 1H nmr (400 MHz, CDCl3) δ1.43 (s, 9H), 2.53 (m, 2H), 3.07-3.14 (m, 1H), 3.30-3.34 (m, 1H), 4.09-4.13 (m, 1H), 4.95 (broad s, 1H), 5.14 (s, 2H), 7.34 (m, 5H).

Workup

  1. extractionextracted into EtOAc (200 ml×2)
  2. washThe combined organics were washed with 1N NaOH (40 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customPurification by Flash 40 chromatography
  8. washeluting with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-9b379e3d2f2e46cea6b896a0d81c9d4c
Source dataset
uspto-grants-2001_10
Patent number
US06306887B1

Reaction notes

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