Acetic Acid → HCID 46946024, compound

HRID 1697495Notes

Reaction equation

HRID 1697495 reaction equation
Cl.[C:2]([CH2:4][NH:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][NH:9]1)=[O:7])#[N:3].C(O)(=O)C.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:2]([CH2:4][NH:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:10][N:9]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:7])#[N:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86646810HCID 86646810, compound

Product 1

HCID 46946024HCID 46946024, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (2S,4R)-4-benzenesulfonyl-pyrrolidine-2-carboxylic acid cyanomethyl-amide hydrochloride (0.13 mmole) prepared in analogy to experiment K1 in THF (1 ml) was added acetic acid (15 ul) followed by the addition of benzaldehyde (0.14 mmole) and stirring was continued at 22° C. for 1 h. Sodium triacetoxyborohydride (0.38 mmole) was added in one portion and stirring was continued at 22° C. for 3 h. The mixture was quenched with aqueous HCL and MeOH and the solution was purified by prep. HPLC (RP-18) using a mixture of acetonitrile and water to give (2S,4R)-4-benzenesulfonyl-1-benzyl-pyrrolidine-2-carboxylic acid cyanomethyl-amide as a colourless oil. MS: 384.1 [M+H]+.

Workup

  1. stirringstirring
  2. waitwas continued at 22° C. for 3 h
  3. customThe mixture was quenched with aqueous HCL and MeOH
  4. customthe solution was purified by prep
  5. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-4d9f45c6cd4e4e788ef6158344fa9995
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…