Phosphoric Acid → [(Tert-butoxy)carbonylamino]-3,4-dihydroxy-N-(phenylmethoxy)butanamide

HRID 527378Notes

Reaction equation

HRID 527378 reaction equation
P(=O)(O)(O)O.[C:6]([O:10][C:11]([NH:13][CH:14]([C:22](=[O:32])[NH:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:15]([OH:21])[C:16](OCC)=[O:17])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(C(C(C(OCC)=O)O)O)(OCC)=O.[BH4-].[Na+].[Na+].[Cl-]>O1CCCC1>[C:6]([O:10][C:11]([NH:13][CH:14]([CH:15]([OH:21])[CH2:16][OH:17])[C:22]([NH:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:32])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 5

HCID 1004Phosphoric Acid2×HCID 5234Sodium ChlorideHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 4311764Sodium borohydrideHCID 86639530ethyl 3-[(tert-butoxy)carbonylamino]-2-hydroxy-3-[N-(phenylmethoxy) carbamoyl]propanoate

Product 1

HCID 86639529[(Tert-butoxy)carbonylamino]-3,4-dihydroxy-N-(phenylmethoxy)butanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To solution of tetrahydrofuran (THF, 6 L) and phosphoric acid buffer (0.025 M, KH2PO4/Na2HPO4; ratio 1/1, 2 L) containing ethyl 3-[(tert-butoxy)carbonylamino]-2-hydroxy-3-[N-(phenylmethoxy) carbamoyl]propanoate (compound prepared from diethyl tartrate according to the procedures described in Org. Synth., Coll. Vol. 1998, 220, J. Org. Chem. 1983, 3556 and U.S. Pat. No. 4,794,108) (120 g, 31.38 mmol), sodium borohydride (59.35 g, 156.9 mmol) was added portion wise at 0° C. over 1 h. The resulting mixture was stirred at 0° C. for an additional 1 h and at room temperature for 2 h. The mixture was cooled at 0° C. before addition of 1M aqueous solution containing H3PO4 until the pH reach 8. NaCl (100 g) was added to the mixture and the organic layer was separated. Extraction with ethyl acetate (3×1.5 L) was performed and the combined organic phases were washed with brine (1 L), dried over MgSO4 and evaporated under vacuo. The residue as purified by column chromatography using hexane/acetone as eluent to get 50 g of white solid.

Workup

  1. customthe organic layer was separated
  2. extractionExtraction with ethyl acetate (3×1.5 L)
  3. washthe combined organic phases were washed with brine (1 L)
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuo
  6. customThe residue as purified by column chromatography

Sources & evidence

ORD record
ord-f365582eb4444b1e9a288444b4b8559a
Source dataset
uspto-grants-2016_05
Patent number
US09346799B2

Reaction notes

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