Sodium borohydride → HCID 20214933, compound

HRID 355201Notes

Reaction equation

HRID 355201 reaction equation
C([O:8][C:9]1[CH:19]=[CH:18][C:17]([C:20](=[O:26])[CH:21](O)OCC)=[CH:16][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])C1C=CC=CC=1.[NH2:27][C:28]([CH3:41])([CH3:40])[CH2:29][CH2:30][N:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[CH:32]1.[BH4-].[Na+]>>[OH:8][C:9]1[CH:19]=[CH:18][C:17]([CH:20]([OH:26])[CH2:21][NH:27][C:28]([CH3:41])([CH2:29][CH2:30][N:31]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=[CH:32]2)[CH3:40])=[CH:16][C:10]=1[NH:11][S:12]([CH3:15])(=[O:13])=[O:14]

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 10317570N-[2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-phenyl]-methanesulphonamideHCID 20214946HCID 20214946, compound

Product 1

HCID 20214933HCID 20214933, compoundYield 81%

Conditions

Temperature
50 °C

Procedure

A mixture of 14.4 gm of 2'-benzyloxy-5'-(1-oxo-2-hydroxy-2-ethoxy-ethyl)-methanesulfonanilide, 7 gm of 1-(3-amino-3-methylbutyl)-benzimidazole and 150 ml of alcohol was heated for 3 hours at 50° C. and then admixed in portions with 9.2 gm of sodium borohydride. The resulting solution is kept for 12 hours at room temperature, the alcohol is then removed under reduced pressure on a Rotavapor, and the residue is dissolved with 200 ml of water and 500 ml of ethyl acetate. After decomposition of the sodium borohydride by stirring with concentrated hydrochloric acid and ice cooling, the mixture was made alkaline with aqueous ammonia, and the ethyl acetate phase was separated, dried with sodium sulfate and evaporated on a Rotavapor. The residue was dissolved in 200 ml of alcohol, the solution was acidified with 6.3 gm of oxalic acid, and the precipitated 2'-benzyloxy-5'-[1-hydroxy-2-[4-(1-benzimiazolyl)-2-methyl-2-butylamino]-ethyl]methane sulfonanilide dioxalate (m.p. 185°-187° C.) is extracted. The base (m.p. 65°-70° C.) was liberated from this compound with aqueous ammonia. Catalytic hydrogenation of this compound (m.p. 65°-70° C.) in 250 ml of methanol under standard conditions with palladium charcoal as a catalyst yielded 8 gm of 2'-hydrox-5'-[1-hydroxy-2-[4-(1-benzimidazolyl)-2-methyl-2-butylamino]-ethyl]-methanesulfonanilide (m.p. 170°-173° C.; 81% of theory) whose formates of the formula ##STR34## had a melting point of 161°-164° C.

Workup

  1. customthe alcohol is then removed under reduced pressure on a Rotavapor
  2. dissolutionthe residue is dissolved with 200 ml of water and 500 ml of ethyl acetate
  3. customthe ethyl acetate phase was separated
  4. dry with materialdried with sodium sulfate
  5. customevaporated on a Rotavapor
  6. dissolutionThe residue was dissolved in 200 ml of alcohol
  7. extractionthe precipitated 2'-benzyloxy-5'-[1-hydroxy-2-[4-(1-benzimiazolyl)-2-methyl-2-butylamino]-ethyl]methane sulfonanilide dioxalate (m.p. 185°-187° C.) is extracted

Sources & evidence

ORD record
ord-3fe3c3ef69d84d7b99745d9bf3596486
Source dataset
uspto-grants-1983_03
Patent number
US04378361

Reaction notes

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