Acetic Acid → HCID 86666035, compound

HRID 469713Notes

Reaction equation

HRID 469713 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[O:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:25][CH:22]2[CH2:23][CH2:24][O:19][CH2:20][CH2:21]2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 54959952(S)-pyrrolidine-2-carboxylic acid (4-tert-butyl-thiazol-2-yl)-amide

Product 1

HCID 86666035HCID 86666035, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid (4-tert-butyl-thiazol-2-yl)-amide; hydrochloride (0.310 g; 1.070 mmol) in 1,2-dichloroethane (2 mL) was added tetrahydro-pyran-4-carbaldehyde (0.244 g; 2.140 mmol), acetic acid (0.2 mL; 3.497 mmol), and sodium sulfate(5-10 equivalents). The mixture is stirred for 30-45 minutes before adding sodium triacetoxyborohydride (0.454 g; 2.140 mmol) and stirring overnight at room temperature. After this time, the mixture is filtered through a plug of silica/Celite® and concentrated in vacuo. Crude material is purified by preparative HPLC. Product fractions are pooled and concentrated in vacuo to afford title compound as an oil. ESI m/z 352 [M+H]+

Workup

  1. stirringstirring overnight at room temperature
  2. filtrationAfter this time, the mixture is filtered through a plug of silica/Celite®
  3. concentrationconcentrated in vacuo
  4. customCrude material is purified by preparative HPLC
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e324db1ce7bf417ebc0942a5182b2070
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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