Water → HCID 14980569, compound

HRID 1590107Notes

Reaction equation

HRID 1590107 reaction equation
[C:1]([CH2:4][S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:7]=1[CH2:24][C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])(O)=[O:2].B.O>C1COCC1>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:8]2[C:9]3[C:14](=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3)[C:6]([S:5][CH2:4][CH2:1][OH:2])=[C:7]2[CH2:24][C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 14980568HCID 14980568, compound

Product 1

HCID 14980569HCID 14980569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the acid from Step 4 (3.8 g, 8.23 mmol) in THF (200 mL) there was added 0.9M borane in THF (25 mL) and the mixture was stirred at r.t. for 1.5 hours. Water (25 mL) was added and the THF removed by evaporation. More H2O was added along with 2N HCl (15 mL) and the mixture was extracted with Et2O 3 times. These extracts were washed with H2O 4 times, dried and evaporated to leave a residue which was chromatographed on silica gel, eluting with a 1:1 mixture of hexane and EtOAc. The title compound was obtained as a thick oil.

Workup

  1. customthe THF removed by evaporation
  2. additionMore H2O was added along with 2N HCl (15 mL)
  3. extractionthe mixture was extracted with Et2O 3 times
  4. washThese extracts were washed with H2O 4 times
  5. customdried
  6. customevaporated
  7. customto leave a residue which
  8. customwas chromatographed on silica gel
  9. washeluting with a 1:1 mixture of hexane and EtOAc

Sources & evidence

ORD record
ord-ce3575a5c11a48c298f09b03ded6d203
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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