Tetrahydrofuran → HCID 86727234, compound

HRID 336338Notes

Reaction equation

HRID 336338 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@@H:17]([O:19][CH3:20])[CH3:18])[C:13](OC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+]>CO>[OH:14][CH2:13][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:17]([O:19][CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 69348486HCID 69348486, compound

Product 1

HCID 86727234HCID 86727234, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-methoxybutanoate (prepared according to the literature procedure: Bioorg. Med. Chem. Lett. 15 (2005) 1447-1449, 1.60 g, 5.68 mmol) in a 3:1 mixture of tetrahydrofuran and methanol (12 mL), sodium borohydride (0.43 g, 11.38 mmol) was added and the mixture was stirred at room temperature for 2 hours. The volatiles were removed and the residue was dissolved in ethyl acetate (25 mL) and washed with brine (10 mL). Removal of the solvent afforded crude product which was purified by silica gel column chromatography using a gradient of ethyl acetate in pet. ether. Yield: 1.32 g (92%). 1H NMR (400 MHz, DMSO-d6) δ: 1.01 (d, 3H), 3.22 (s, 3H), 3.36-3.42 (m, 3H), 3.57-3.60 (m, 1H), 4.57 (t, 1H), 5.02 (s, 2H), 6.98-7.01 (m, 1H), 7.31-7.37 (m, 5H). MS (ES) MH+: 254.4 for C13H19F3NO4.

Workup

  1. additionwas added
  2. customThe volatiles were removed
  3. dissolutionthe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with brine (10 mL)
  5. customRemoval of the solvent
  6. customafforded crude product which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e83fb8f13b424957a02c2942b9b0a7d7
Source dataset
uspto-grants-2014_11
Patent number
US08889671B2

Reaction notes

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