Hydrochloric Acid → HCID 15157490, compound

HRID 2371634Notes

Reaction equation

HRID 2371634 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:9]2[CH:10]=[CH:11][C:12]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:13]([CH2:14][CH2:15][CH3:16])[C:8]=2[O:7][C:6]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:5]1.Cl>O.O1CCCC1>[OH:3][CH:4]1[C:9]2[CH:10]=[CH:11][C:12]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:13]([CH2:14][CH2:15][CH3:16])[C:8]=2[O:7][C:6]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15157434HCID 15157434, compound

Product 1

HCID 15157490HCID 15157490, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 78 mg (2.1 mmol) of NaBH4 in 2 ml of water at 0° C. is added over 3 minutes a solution of 250 mg (0.515 mmol) of the title product of Example 17 in 3 ml of tetrahydrofuran (THF). After 30 minutes at 0° C., the mixture was permitted to warm to room temperature, and a further 2 ml each of water and of THF were added. After one hour, the reaction mixture was acidified with 3N hydrochloric acid, and the mixture was extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), the drying agent removed by filtration, and the solvent removed under reduced pressure. Crystallization of the residue from 50% ethyl acetate/hexane gave the title compound (150 mg), m.p. 131.5°-132.5° C.

Workup

  1. waitAfter one hour
  2. extractionthe mixture was extracted with three portions of ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe drying agent removed by filtration
  6. customthe solvent removed under reduced pressure
  7. customCrystallization of the residue from 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-660b13a37cf240c2b0ddff3ac9a28312
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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