tert-butyl N-(2-oxoethyl)carbamate → HCID 67344764, compound

HRID 1669437Notes

Reaction equation

HRID 1669437 reaction equation
[CH2:1]([NH:8][C@@H:9]1[CH2:16][N:15]2[C:17]3[CH:18]=[C:19]([C:30]([O:32][CH3:33])=[O:31])[CH:20]=[CH:21][C:22]=3[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:14]2[C:13]2[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:12]=2[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].[C:43]([NH:50][CH2:51][CH:52]=O)([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CO.CC(O)=O>[CH2:1]([N:8]([CH2:52][CH2:51][NH:50][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@@H:9]1[CH2:16][N:15]2[C:17]3[CH:18]=[C:19]([C:30]([O:32][CH3:33])=[O:31])[CH:20]=[CH:21][C:22]=3[C:23]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[C:14]2[C:13]2[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:12]=2[O:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 67346582HCID 67346582, compound

Product 1

HCID 67344764HCID 67344764, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To the solution of methyl (7R)-7-(benzylamino)-14-cyclohexyl-3-fluoro-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate in MeOH/HOAc containing NaCNBH3 from the previous step was added N-Boc-2-aminoacetaldehyde (1.5 eq) and the solution was stirred at RT. After 1 h all volatiles were evaporated. The residual material was taken up with EtOAc and the resulting solution was washed with sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The yellow residue was subjected to FC (PE:EtOAc, 8:2+1% NEt3). After evaporation of the solvents the product was obtained as a colourless solid (71%). (ES+) m/z 656 (M+H)+.

Workup

  1. customAfter 1 h all volatiles were evaporated
  2. washthe resulting solution was washed with sat. aq. NaHCO3 and brine
  3. dry with materialAfter drying over Na2SO4 all volatiles
  4. customwere evaporated in vacuo
  5. customAfter evaporation of the solvents the product

Sources & evidence

ORD record
ord-30ec72bd126a420c88c959aeefcbcc28
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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