Acetic Acid → HCID 54579374, compound

HRID 1942761Notes

Reaction equation

HRID 1942761 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][CH2:10][CH:11]=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[S:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:25]=2)[C:23]#[N:24])=[N:15][CH:14]=1)[CH3:2].[NH:30]1[CH2:33][CH:32]([C:34]([OH:36])=[O:35])[CH2:31]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:23]([C:22]1[CH:25]=[C:18]([C:16]2[S:17][C:13]([C:4]3[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][CH2:10][CH2:11][N:30]4[CH2:33][CH:32]([C:34]([OH:36])=[O:35])[CH2:31]4)[CH:7]=[CH:6][CH:5]=3)=[CH:14][N:15]=2)[CH:19]=[CH:20][C:21]=1[O:26][CH:27]([CH3:29])[CH3:28])#[N:24]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 58494021HCID 58494021, compound

Product 1

HCID 54579374HCID 54579374, compoundYield 44%

Procedure

A solution of 5-{5-[2-ethyl-3-(3-oxopropyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methyl ethyl)oxy]benzonitrile (D115) (150 mg, 0.371 mmol), 3-azetidinecarboxylic acid (75.0 mg, 0.742 mmol) and acetic acid (0.1 ml, 1.747 mmol) was stirred at room temperature for 15 min, then sodium triacetoxyborohydride (236 mg, 1.112 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 concentrated and purified by Mass Directed AutoPrep to afford 1-{3-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-2-ethyl phenyl]propyl}-3-azetidinecarboxylic acid (E93) (80 mg) as a TFA salt.

Workup

  1. concentrationAfter concentration
  2. customthe residue was partitioned between ethyl acetate and aqueous HCl (2M)
  3. concentrationThe organic phase was concentrated
  4. custompurified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-332a1b05a7d74fbdbb9b3a3fca5c48dd
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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