HCID 11279349, compound → HCID 86694364, compound

HRID 538933Notes

Reaction equation

HRID 538933 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C@@H:12]([CH3:16])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[OH:14][CH2:13][C@@H:12]([N:11]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:16]

Participants

3

Reactant 1

HCID 11279349HCID 11279349, compound

Product 1

HCID 86694364HCID 86694364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (S)-2-(((benzyloxy)carbonyl)(4-methoxybenzyl)amino)propanoic acid [439589-23-8] (16 g, 41.9 mmol) in THF (150 mL) was slowly added under argon borane dimethylsulfide (8.4 mL, 84 mmol) at 0-5° C. The reaction mixture was stirred for 1 h at 0-5° C. followed by 3 h at 40-45° C. Excess borane was destroyed by careful addition of MeOH and the reaction mixture was evaporated 3× with 200 mL MeOH and 2× with CHCl3. The title compound was obtained after drying as a colorless oil (13.7 g, 99%): TLC (hexane/EtOAc 1:1) Rf=0.22; tR=1.06 min (UPLC 1), tR, 1.02 min (LC-MS 3); ESI-MS: 330 [M+H]+ (LC-MS 3).

Workup

  1. waitfollowed by 3 h at 40-45° C
  2. customExcess borane was destroyed by careful addition of MeOH
  3. customthe reaction mixture was evaporated 3× with 200 mL MeOH and 2× with CHCl3

Sources & evidence

ORD record
ord-3946d7e4fd1a4230a972822e8d2c22d1
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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