Methanol → HCID 59557723, compound

HRID 1175310Notes

Reaction equation

HRID 1175310 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[C:23]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)[C:22]([Cl:34])=[CH:21][C:20]=2[CH2:35][CH2:36][O:37][CH2:38][CH:39]=[O:40])[O:7][C@@H:6]1[CH2:41][O:42][C:43](=[O:45])[CH3:44])(=[O:3])[CH3:2].[BH4-].[Na+].CO>C1COCC1>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[C:23]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)[C:22]([Cl:34])=[CH:21][C:20]=2[CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40])[O:7][C@@H:6]1[CH2:41][O:42][C:43](=[O:45])[CH3:44])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59557711HCID 59557711, compound

Product 1

HCID 59557723HCID 59557723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-5-(4-ethylbenzyl)-2-(2-(2-oxoethoxy)ethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (25 mg, 0.039 mmol) and NaBH4 (5.5 mg, 0.145 mmol) in THF (0.8 mL), was added MeOH (0.03 mL) dropwise. After being stirred for 1 h at the same temperature, the reaction was quenched by addition of saturated NH4Cl. The mixture was extracted 3× with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. Concentration gave the pure product in quantitative yield. MS ESI (m/z) 649 (M+1)+, calc. 648.

Workup

  1. customthe reaction was quenched by addition of saturated NH4Cl
  2. extractionThe mixture was extracted 3× with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration
  6. customgave the pure product in quantitative yield

Sources & evidence

ORD record
ord-ceaf1060c2724053b4e5401aad9adfe9
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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