Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216930Notes

Reaction equation

HRID 216930 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:23][C:24]([C:26]1([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:22]=[CH:21][C:14]3[O:15][CH2:16][C:17](=[O:20])[N:18]([CH3:19])[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:2]([C@@H:3]([NH:23][C:24]([C:26]1([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:22]=[CH:21][C:14]3[O:15][CH2:16][C:17](=[O:20])[N:18]([CH3:19])[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568612(S)-tert-Butyl 4-(1-amino-3-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568576(S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 10, step (iii), 155 mg) in dichloromethane (8 mL) was stirred at room temperature for 18 h with Burgess' reagent (134 mg). The solvent was partially evaporated and the mixture was absorbed onto silica for purification on a silica column using ethyl acetate/isohexane 1:1 as eluent to yield the sub-titled compound as a solid (156 mg).

Workup

  1. customThe solvent was partially evaporated
  2. customthe mixture was absorbed onto silica for purification on a silica column

Sources & evidence

ORD record
ord-bf0948e360df442aad8572b7cf7f8d11
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

Loading…