3-Bromo-1-propanol → HCID 21099362, compound

HRID 1351417Notes

Reaction equation

HRID 1351417 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:21][CH2:22][CH2:23][CH2:24]O>C(Cl)Cl>[Br:21][CH2:22][CH2:23][CH2:24][O:19][C:18](=[O:20])[C@H:9]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 123083-Bromo-1-propanolHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

Product 1

HCID 21099362HCID 21099362, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-Boc-Homophenylalanine (5.00 g, 17.9 mmol) and 3-bromo-1-propanol (1.60 mL, 17.7 mmol) were dissolved in CH2Cl2 (25 mL) and the mixture was cooled to 0° C. A solution of N,N-dicyclohexylcarbodiimide (4.80 g, 23.3 mmol) and N,N-dimethylaminopyridine (0.23 g, 1.90 mmol) in CH2Cl2 (25 mL) was slowly added and the reaction was slowly warmed to room temperature and stirred for 12 hours. The dicyclohexylurea was filtered off and the mother liquor was concentrated and purified by flash chromatography (Hexane/EtOAc 8:2) affording N-Boc-Homophenylalanine 3-bromopropyl ester as a clear oil (5.64 g, 79%).

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. filtrationThe dicyclohexylurea was filtered off
  3. concentrationthe mother liquor was concentrated
  4. custompurified by flash chromatography (Hexane/EtOAc 8:2)

Sources & evidence

ORD record
ord-18e98f05c1dc4effa11db72b9fff318f
Source dataset
uspto-grants-2007_05
Patent number
US07217733B2

Reaction notes

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