Acetic Acid → HCID 18784744, compound

HRID 1636722Notes

Reaction equation

HRID 1636722 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]3=[O:30])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[C:33](O)(=O)[CH3:34].[CH3:37]O.[CH2:39]1[CH2:43]O[CH2:41][CH2:40]1>>[C:2]1([CH:1]([O:8][CH2:37][C:33]2[CH:34]=[CH:43][CH:39]=[CH:40][CH:41]=2)[C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:16][CH2:17][CH:18]([N:21]4[CH2:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:22]4=[O:30])[CH2:19][CH2:20]3)=[CH:13][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 9930637HCID 9930637, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 18784744HCID 18784744, compoundYield 71%

Conditions

Temperature
0 °C

Procedure

To a solution of Example 280 compound (500 mg, 1.26 mmol) in MeOH/THF (1:1)(30 mL) at 0° C. was added sodium borohydride (48 mg, 1.26 mmol). The reaction was stirred at 0° C. for 2 hours then warmed to RT overnight. Acetic acid was added to quench the reaction until the reaction was pH 6 by pH paper. The resulting mixture was evaporated to dryness. Ethyl ether (200 mL) was added to the residue, and the organic layer was washed with water (2×50 mL), saturated sodium bicarbonate solution (2×50 mL), brine (2×50 mL) and dried over MgSO4. Evaporation gave title compound (355 mg, 71%) as a crude oil.

Workup

  1. temperaturethen warmed to RT overnight
  2. customto quench
  3. customthe reaction until the reaction
  4. customThe resulting mixture was evaporated to dryness
  5. additionEthyl ether (200 mL) was added to the residue
  6. washthe organic layer was washed with water (2×50 mL), saturated sodium bicarbonate solution (2×50 mL), brine (2×50 mL)
  7. dry with materialdried over MgSO4
  8. customEvaporation

Sources & evidence

ORD record
ord-eb018dc4d9454734aff380f026a9b674
Source dataset
uspto-grants-2000_03
Patent number
US06034098

Reaction notes

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