Acetic Acid → HCID 59843223, compound

HRID 2196533Notes

Reaction equation

HRID 2196533 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[O:15])=[CH:12][C:11]([C:26]([F:29])([F:28])[F:27])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:30][N:31]([CH2:39][CH:40]=O)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:14]([C:13]1[N:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH2:2][NH:1][CH2:40][CH2:39][N:31]([CH3:30])[C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[N:10]=[C:11]([C:26]([F:28])([F:29])[F:27])[CH:12]=1)=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 59843177HCID 59843177, compound

Product 1

HCID 59843223HCID 59843223, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 58 (200 mg, 0.386 mmol) in MeOH (2.0 mL) was added tert-butyl methyl(2-oxoethyl)carbamate (100 mg, 0.579 mmol) followed by acetic acid (44.2 μl, 0.772 mmol). After stirring for 30 min, sodium cyanoborohydride (61 mg, 0.964 mmol) was added and the resulting solution was allowed to stir at 21° C. for 16 h. The solvent was removed by evaporation and the residue taken in saturated NaHCO3. It was then extracted three times with CH2Cl2, dried over Na2SO4 and evaporated. The residue was purified via silica gel flash chromatography (40% to 100% EtOAc/hexanes). The title product 59 (81 mg, 37% yield) was isolated as a yellow solid. LRMS (ESI): calc. 561.6; found 562.7 (MH)+.

Workup

  1. stirringto stir at 21° C. for 16 h
  2. customThe solvent was removed by evaporation
  3. extractionIt was then extracted three times with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified via silica gel flash chromatography (40% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-969ce5d2b259484699513427f5d95280
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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