1,2-Dichloroethane → HCID 10182672, compound

HRID 1057737Notes

Reaction equation

HRID 1057737 reaction equation
[CH3:1][C:2]([C:5]1[O:9][C:8]([CH2:10][S:11][C:12]2[S:16][C:15]([NH:17][C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[O:19])=[N:14][CH:13]=2)=[N:7][CH:6]=1)([CH3:4])[CH3:3].[O:26]=[CH:27][CH:28]([CH2:30]O)[OH:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCCl>CO>[OH:29][CH:28]([CH2:27][OH:26])[CH2:30][N:23]1[CH2:22][CH2:21][CH:20]([C:18]([NH:17][C:15]2[S:16][C:12]([S:11][CH2:10][C:8]3[O:9][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:6][N:7]=3)=[CH:13][N:14]=2)=[O:19])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 751GlyceraldehydeHCID 3025986BMS 387032HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10182672HCID 10182672, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[5-[[[5-(1,1-Dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide (66 mg, 0.17 mmol, 1 eq) was combined with glyceraldehyde (69 mg, 0.77 mmol, 4.5 eq), sodium triacetoxyborohydride (163 mg, 0.77 mmol, 4.5 eq) and 1,2-dichloroethane (4 mL). The resulting suspension was stirred at rt for 4 h. Methanol (1 mL) was added and the reaction mixture was stirred at rt overnight, concentrated in vacuo and purified by preparative HPLC to provide 69 mg (59%) of (±)-1-(2,3-dihydroxypropyl)-N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide as a white solid. MS: 455 [M+H]+; HPLC: 100% at 3.06 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. stirringthe reaction mixture was stirred at rt overnight
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d540c7a820144d3a850f8ca0420c6d89
Source dataset
uspto-grants-2003_02
Patent number
US06515004B1

Reaction notes

Loading…