Acetic Acid → HCID 68863070, compound

HRID 229123Notes

Reaction equation

HRID 229123 reaction equation
COC(=O)CC1C=CC=C(O[CH2:12][C@H:13]([CH3:30])[CH2:14][NH:15][CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)C=1.[CH:32]([C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)([CH3:34])[CH3:33].C([BH3-])#N.[Na+].[OH-:47].[Na+].[C:49]([OH:52])(=[O:51])[CH3:50]>CO.O>[C:24]1([CH:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][N:15]([C@H:14]([O:47][C:18]2[CH:19]=[C:20]([CH2:50][C:49]([OH:52])=[O:51])[CH:21]=[CH:22][CH:23]=2)[CH:13]([CH3:12])[CH3:30])[CH2:39][C:38]2[CH:41]=[CH:42][C:35]([CH:32]([CH3:34])[CH3:33])=[CH:36][CH:37]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 326CuminaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 68862426HCID 68862426, compound

Product 1

HCID 68863070HCID 68863070, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of {3-[(R)-3-(2,2-diphenyl-ethylamino)-2-methyl-propoxy]-phenyl}-acetic acid methyl ester (100 mg, 240 μmol) in methanol (1 mL) was added acetic acid (10% by volume) followed by 4-isopropyl-benzaldehyde (106 mg, 719 μmol) and sodium cyanoborohydride (44.5 mg, 719 μmol). After the resulting mixture was stirred for 18 h at RT, water was added to the reaction mixture. The solution was made basic by the addition of sodium hydroxide and heated for 30 min. The sample concentrated and was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile: H2O, UV detection at 254 nm) to give the title compound as a solid (49.9 mg, 39%). MS (ESI) 535 (M+H)+.

Workup

  1. temperatureheated for 30 min
  2. concentrationThe sample concentrated
  3. customwas purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile: H2O, UV detection at 254 nm)

Sources & evidence

ORD record
ord-d191b5742b0e47e7ad697a464e489b4d
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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