Disodium 2,3-dihydroxybutanedioate → HCID 69465121, compound

HRID 1794562Notes

Reaction equation

HRID 1794562 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[CH3:19][C@@H:20]([C:36](=[O:43])[C@@H:37]([CH3:42])[C@H:38]([OH:41])[CH2:39][CH3:40])[C:21]([N:23]1[C@@H:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:26][O:25][C:24]1=[O:35])=[O:22].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(#N)C>[CH3:19][C@@H:20]([C@@H:36]([OH:43])[C@@H:37]([CH3:42])[C@H:38]([OH:41])[CH2:39][CH3:40])[C:21]([N:23]1[C@@H:27]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:26][O:25][C:24]1=[O:35])=[O:22]

Participants

6

Reactant 3

HCID 13355Disodium 2,3-dihydroxybutanedioateHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 56985563HCID 56985563, compound

Product 1

HCID 69465121HCID 69465121, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Tetramethylammonium triacetoxyborohydride (2.89 g) was dissolved in a mixture of acetic acid (11 ml) and acetonitrile (11 ml), stirred for 30 minutes at ambient temperature, then cooled to −15° C. before addition of (4S)-N-[(2S,4S,5R)-2,4-dimethyl-5-hydroxy-3-oxoheptanoyl]-4-benzyl-2-oxazolidinone (0.764 g). After stirring for 4 hours, 34 ml of 0.5 M sodium tartrate was added and stirring was continued for an additional 3 hours. After extraction with 3 portions of CH2Cl2, the organic phases were combined and dried over MgSO4. The solvent was removed under vacuum, and the crude product was evaporated 3 times from 50 ml of methanol to yield 0.644 g of product (84%).

Workup

  1. stirringAfter stirring for 4 hours
  2. stirringstirring
  3. waitwas continued for an additional 3 hours
  4. extractionAfter extraction with 3 portions of CH2Cl2
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under vacuum
  7. customthe crude product was evaporated 3 times from 50 ml of methanol

Sources & evidence

ORD record
ord-92ba16625eae40769e9d9322c8576213
Source dataset
uspto-grants-2006_04
Patent number
US07022825B2

Reaction notes

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