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Hydrochloric Acid → N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamide

HRID 1618326
Notes
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Reaction equation

HRID 1618326 reaction equation
C([O:3][C:4](=O)[C:5]([NH:27][C:28](=[O:30])[CH3:29])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=1)[C:6](OCC)=[O:7])C.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>O.C(O)C>[OH:3][CH2:4][C:5]([NH:27][C:28](=[O:30])[CH3:29])([CH2:6][OH:7])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 98457531,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioate

Product 1

HCID 10521783N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamideYield 101.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962WaterSolvent

Procedure

28 g (64.57 mmole) 2-(acetylamino)-2-[2(4-octylphenyl)ethyl]propanedioic acid diethylester (=compound according to formula (III)) was added to 450 ml ethanol. A solution of 17.91 g calcium chloride in 125 ml water was added in one lot. 12.21 g (322.7 mmole) sodium borohydride was added to the reaction mixture at 0° C. in 1 hr 20 min. The reaction mixture was left overnight for stirring. 100 ml of 1 N HCl was added to neutralize the reaction mixture and inorganic solids were filtered and washed with 200 ml ethanol. Filtrate was evaporated under vacuum. 300 ml water was added to the residue obtained and was extracted with 2×250 ml EtOAC. The organic extract was washed with brine, dried over sodium sulphate and evaporated to give 23 g semisolid.

Workup

  1. filtrationwere filtered
  2. washwashed with 200 ml ethanol
  3. customFiltrate was evaporated under vacuum
  4. addition300 ml water was added to the residue
  5. customobtained
  6. extractionwas extracted with 2×250 ml EtOAC
  7. extractionThe organic extract
  8. washwas washed with brine
  9. dry with materialdried over sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-8a64edb22f7c4a09bd5e97caf9ec1496
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08766005B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes