Citric Acid → HCID 90060275, compound

HRID 1779243Notes

Reaction equation

HRID 1779243 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[BH4-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([OH:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 90060203HCID 90060203, compound

Product 1

HCID 90060275HCID 90060275, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

No. 5233427 (14.4 mg, 0.022 mmol) was dissolved in methanol (1.0 mL), and the solution was cooled to 0° C. in an ice bath. Sodium tetrahydroborate (5 mg, 0.13 mmol) was added, and the mixture was stirred for 3 hours. The progress of the reaction was stopped by adding water, and the mixture was diluted in ethyl acetate. An aqueous solution of 0.5 M citric acid was added and the mixture was separated. The separated organic layer was washed with water and a saturated brine in order, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated. The residue was purified by diol thin layer chromatography (dichloromethane:methanol=50 50) to obtain the target compound at a yield of 57%.

Workup

  1. customthe mixture was separated
  2. washThe separated organic layer was washed with water
  3. dry with materiala saturated brine in order, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by diol thin layer chromatography (dichloromethane:methanol=50 50)
  7. customto obtain the target compound at a yield of 57%

Sources & evidence

ORD record
ord-104afe985a2d46e3bbc00c6c1e5f54cb
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…