Acetic Acid → HCID 54579141, compound

HRID 1942760Notes

Reaction equation

HRID 1942760 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][CH:10]=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([C:17]2[CH:18]=[CH:19][C:20]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH:24]=2)[C:22]#[N:23])=[N:14][CH:13]=1)[CH3:2].[NH:29]1[CH2:36][CH2:35][CH2:34][C@H:30]1[C:31]([OH:33])=[O:32].C(O)(=O)C.C([BH3-])#N.[Na+]>>[C:22]([C:21]1[CH:24]=[C:17]([C:15]2[S:16][C:12]([C:4]3[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][CH2:10][N:29]4[CH2:36][CH2:35][CH2:34][C@H:30]4[C:31]([OH:33])=[O:32])[CH:7]=[CH:6][CH:5]=3)=[CH:13][N:14]=2)[CH:18]=[CH:19][C:20]=1[O:25][CH:26]([CH3:28])[CH3:27])#[N:23]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 145742L-ProlineHCID 5003444Sodium cyanoborohydrideHCID 866590085-{5-[2-Ethyl-3-(2-oxoethyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methylethyl)oxy]benzonitrile

Product 1

HCID 54579141HCID 54579141, compoundYield 14.6%

Procedure

A solution of 5-{5-[2-ethyl-3-(2-oxoethyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methylethyl) oxy]benzonitrile (D76) (60 mg, 0.154 mmol), L-proline (35.4 mg, 0.307 mmol) and acetic acid (0.1 ml, 1.747 mmol) was stirred at room temperature for 15 min, then sodium cyanoborohydride (29.0 mg, 0.461 mmol) was added. The mixture was stirred at room temperature for 2 h. After concentration, the residue was partitioned between ethyl acetate and aqueous HCl (2M). The organic phase was washed with saturated brine, concentrated and purified by Mass Directed AutoPrep to afford 1-{2-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-2-ethylphenyl]ethyl}-L-proline (E88) (11 mg) as a TFA salt.

Workup

  1. concentrationAfter concentration
  2. customthe residue was partitioned between ethyl acetate and aqueous HCl (2M)
  3. washThe organic phase was washed with saturated brine
  4. concentrationconcentrated
  5. custompurified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-ba22592596b44926b86d2087ee639e5c
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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