Sodium Carbonate → HCID 3077194, compound

HRID 1533986Notes

Reaction equation

HRID 1533986 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[CH:21][NH:22]2)=[O:17])([CH3:4])[CH3:3].[BH4-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH3:4][C:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([C:18]1[C:19]2[CH:20]=[CH:21][NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)[OH:17])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3077190HCID 3077190, compoundHCID 4311764Sodium borohydride

Product 1

HCID 3077194HCID 3077194, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 5.25 g of the product of Step F of Example 3, 70 ml of normal butanol and 1.7 g of sodium borohydride was stirred at reflux for one hour and the mixture was cooled. 200 ml of a saturated solution of sodium carbonate were added and extraction was carried out with an ethyl acetate-tetrahydrofuran mixture. The extracts were evaporated to dryness under reduced pressure and after chromatography on silica (eluant: ethyl acetate-triethylamine (95-5)), 5.0 g of product melting at 205° C. were obtained. 4.3 g of the product were crystallized from 580 ml of acetonitrile to obtain 3.78 g of the desired product melting at 205° C.

Workup

  1. temperatureat reflux for one hour
  2. temperaturethe mixture was cooled
  3. extractionextraction
  4. customThe extracts were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-82d61b83f5014233b2f9ec1c7be6467b
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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