Acetic Acid → HCID 59563519, compound

HRID 2090248Notes

Reaction equation

HRID 2090248 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1)=O.[CH2:14]([C:18]1[N:19]([CH2:32][CH2:33][CH2:34][NH:35][CH:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:20]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([NH2:30])[C:21]=2[N:31]=1)[CH2:15][CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CN1C(=O)CCC1.CO>[NH2:30][C:22]1[C:21]2[N:31]=[C:18]([CH2:14][CH2:15][CH2:16][CH3:17])[N:19]([CH2:32][CH2:33][CH2:34][N:35]([CH2:1][C:3]3[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=3)[CH:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)[C:20]=2[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 68432258HCID 68432258, compound

Product 1

HCID 59563519HCID 59563519, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of methyl 2-(3-formylphenyl)acetate (0.15 g) dissolved in NMP (10 mL) was added to a stirred solution of the product from step (i) (0.36 g) in NMP (10 mL) at rt. Sodium triacetoxyborohydride (0.90 g) was added to the mixture, the temperature was increased to 50° C. and the reaction mixture stirred for 24 h. The resulting solution was dissolved in methanol (0.5 mL), acidified with acetic acid (0.5 mL) and purified by SCX. The crude product was further purified by RPHPLC to give the title product, yield 22 mg.

Workup

  1. custompurified by SCX
  2. customThe crude product was further purified by RPHPLC

Sources & evidence

ORD record
ord-bdaa2b19fe62486b84bac2f0829f324f
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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