Acetic Acid → HCID 68431610, compound

HRID 2090249Notes

Reaction equation

HRID 2090249 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=O.[CH2:13]([C:17]1[N:18]([CH2:31][CH2:32][CH2:33][NH:34][CH:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)[C:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[C:21]([NH2:29])[C:20]=2[N:30]=1)[CH2:14][CH2:15][CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CN1C(=O)CCC1.CO>[NH2:29][C:21]1[C:20]2[N:30]=[C:17]([CH2:13][CH2:14][CH2:15][CH3:16])[N:18]([CH2:31][CH2:32][CH2:33][N:34]([CH2:1][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=3)[CH:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)[C:19]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 113441872-(4-formylphenyl)acetic AcidHCID 68432258HCID 68432258, compound

Product 1

HCID 68431610HCID 68431610, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
50 °C

Procedure

A solution of 2-(4-formylphenyl)acetic acid (0.14 g) dissolved in NMP (10 mL) was added to a stirred solution of the product from example 8 step (i) (0.34 g) in NMP (10 mL) at rt. Sodium triacetoxyborohydride (0.90 g) was added and the mixture heated at 50° C. for 24 h. The resulting solution was dissolved in methanol (0.5 mL), acidified with acetic acid (0.5 mL) and and purified by SCX. The crude product was further purified by RPHPLC to give the subtitle product, yield 0.25 g.

Workup

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

Sources & evidence

ORD record
ord-12f8d6347ace43bf9f66d49d3841409f
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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