4-(Benzyloxy)butan-2-one → 5-(2-(4-Benzyloxy-2-Butylamino)-1-Hydroxyethyl)Salicylamide

HRID 1701862Notes

Reaction equation

HRID 1701862 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11](=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH:16]([C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1)[OH:17].C([BH3-])#N.[Na+]>>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:14][CH2:15][CH:16]([C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1)[OH:17])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2345114-(Benzyloxy)butan-2-oneHCID 5003444Sodium cyanoborohydrideHCID 155656635-(2-Amino-1-hydroxyethyl)-2-hydroxybenzamide

Product 1

HCID 131169065-(2-(4-Benzyloxy-2-Butylamino)-1-Hydroxyethyl)Salicylamide

Procedure

Combine 4-benzyloxy-2-butanone (2.6 g, 15 mmol) with 5-(2-amino-1-hydroxyethyl)salicylamide (15 mmol in methanol, 50 ml) and treat with sodium cyanoborohydride (0.9 g, 15 mmol). Let stand 16 hours, evaporate the solvent and extract the residue in ethyl acetate/ 1N sodium bicarbonate solution. Separate the organic phase, dry over sodium sulfate and evaporate in vacuo.

Workup

  1. customevaporate the solvent
  2. extractionextract the residue in ethyl acetate/ 1N sodium bicarbonate solution
  3. customSeparate the organic phase
  4. dry with materialdry over sodium sulfate
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-e42f7afc30964c418d0f3ed2049021d2
Source dataset
uspto-grants-1983_04
Patent number
US04379166

Reaction notes

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