Water → HCID 9891401, compound

HRID 1953221Notes

Reaction equation

HRID 1953221 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH2:6][N:7]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:8]1([C:14](=[O:17])[NH:15][OH:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)C.C1(C)C=CC=CC=1.O.[OH-].[Na+]>ClCCl>[F:34][C:31]1[CH:30]=[CH:29][C:28]([O:27][C:24]2[CH:23]=[CH:22][C:21]([S:18]([N:7]([C:8]3([C:14](=[O:17])[NH:15][OH:16])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[CH2:6][CH2:5][C:4]([OH:35])=[O:3])(=[O:19])=[O:20])=[CH:26][CH:25]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 9936129HCID 9936129, compound

Product 1

HCID 9891401HCID 9891401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 15.1 mmoles of the product from Step G in dichloromethane is concentrated by rotary evaporation with the addition of 75 mL of toluene. This solution is treated with 75 mL of water, cooled to 0° C., and treated with 6.05 g (151 mmol, 10 equivalents) of sodium hydroxide pellets over 10 minutes with vigorous stirring. This mixture is stirred for 15 minutes at 0° C. and warmed to ambient temperature over one hour. The aqueous phase is separated, diluted with 7.5 mL of tetrahydrofuran, cooled to 0° C., and treated with 33 mL of 6N aqueous hydrochloric acid over 20 minutes. This mixture is stirred with 75 mL of ethyl acetate at 0° C. to ambient temperature, and the ethyl acetate phase is separated and washed with water. The ethyl acetate solution was concentrated to yield the title compound.

Workup

  1. temperaturewarmed to ambient temperature over one hour
  2. customThe aqueous phase is separated
  3. additiondiluted with 7.5 mL of tetrahydrofuran
  4. temperaturecooled to 0° C.
  5. additiontreated with 33 mL of 6N aqueous hydrochloric acid over 20 minutes
  6. stirringThis mixture is stirred with 75 mL of ethyl acetate at 0° C. to ambient temperature
  7. customthe ethyl acetate phase is separated
  8. washwashed with water
  9. concentrationThe ethyl acetate solution was concentrated

Sources & evidence

ORD record
ord-eb98f512c9fd45dbb67041c298aaf2b7
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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