Water → HCID 13576825, compound

HRID 1252174Notes

Reaction equation

HRID 1252174 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]4[CH:19]5[CH:23]([CH2:24][C:12]([C:13]=34)=[CH:11]2)[N:22]([CH3:25])[CH2:21][CH:20]5[C:26](OC)=[O:27])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>CO>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]4[CH:19]5[CH:23]([CH2:24][C:12]([C:13]=34)=[CH:11]2)[N:22]([CH3:25])[CH2:21][CH:20]5[CH2:26][OH:27])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 13576813HCID 13576813, compound

Product 1

HCID 13576825HCID 13576825, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of the 9-methyl ester (Example 14) (0.365 g) in dry methanol (4 cm3) under anhydrous conditions was added sodium borohydride (0.252 g) causing vigorous effervescence. After 2 hours further sodium borohydride (0.067 g) was added. After the initial effervescence had subsided the reaction was heated to 60° C. Reaction was indicated to be complete and after 4 hours water (4 cm3) was carefully added and the cloudy mixture allowed to cool to room temperature. The product was extracted from the aqueous solution with chloroform, the combined extract washed with water (50 cm3), dried and evaporated under vacuum to yield the title compound as a yellow-white foam, m.p. 124°-127° C.

Workup

  1. customReaction
  2. temperatureto cool to room temperature
  3. extractionThe product was extracted from the aqueous solution with chloroform
  4. extractionthe combined extract
  5. washwashed with water (50 cm3)
  6. customdried
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-9f15a56c5f3d429b9792a85e013b321a
Source dataset
uspto-grants-1988_05
Patent number
US04742075

Reaction notes

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