Methanol → 3-Benzyloxycarbonylamino-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

HRID 2075810Notes

Reaction equation

HRID 2075810 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:9](=O)[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C[OH:38]>>[C:1]([O:5][C:6](=[O:34])[CH:7]([OH:38])[CH:8]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:9][CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 865944013-Benzyloxycarbonylamino-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Product 1

HCID 866130753-Benzyloxycarbonylamino-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl esterYield 81%

Procedure

To a dry round bottom flask equipped with a magnetic stir bar was added composition 12 (189 mg, 0.38 mM, 1 equiv) and MeOH (20 mL). With constant stirring was added NaBH4 (8 mg, 0.228 mmol, 0.6 equiv). Upon addition gas bubbles were produced and the resulting clear colorless solution was stirred at 0° C. for 30 minutes. Solvent was removed in vacuo and the resulting solid was purified via column chromatography (silica gel, 2:1, hexanes/EtOAc) to give 13 as a sticky white solid. (165 mg, 0.34 mmol, 81% yield) ESMS: 488.2 (M+H+), 510.8 (M+Na+).

Workup

  1. customTo a dry round bottom flask equipped with a magnetic stir bar
  2. additionUpon addition gas bubbles
  3. customwere produced
  4. stirringthe resulting clear colorless solution was stirred at 0° C. for 30 minutes
  5. customSolvent was removed in vacuo
  6. customthe resulting solid was purified via column chromatography (silica gel, 2:1, hexanes/EtOAc)

Sources & evidence

ORD record
ord-f85776ebc8e84e2bb623f9088fd31f24
Source dataset
uspto-grants-2011_04
Patent number
US07923433B2

Reaction notes

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