Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216968Notes

Reaction equation

HRID 216968 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:12]=[CH:13][C:14]3[N:19]([CH3:20])[C:18](=[O:21])[CH2:17][S:16][C:15]=3[CH:22]=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:12]=[CH:13][C:14]3[N:19]([CH3:20])[C:18](=[O:21])[CH2:17][S:16][C:15]=3[CH:22]=2)=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568625(S)-tert-Butyl 4-(1-amino-3-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568616(S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 89.8%

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]thiazin-7-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 28, step (ii), 138 mg) in dichloromethane (10 mL) was treated with Burgess' reagent (116 mg) and stirred at room temperature for 18 h. The solvent was partially evaporated and the residue absorbed onto silica and purified by chromatography on silica eluting with ethyl acetate/isohexane (50:50 to 70:30) to afford the sub-titled compound (120 mg).

Workup

  1. customThe solvent was partially evaporated
  2. customthe residue absorbed onto silica
  3. custompurified by chromatography on silica eluting with ethyl acetate/isohexane (50:50 to 70:30)

Sources & evidence

ORD record
ord-c8f0055a97074f7dadfe405badef11df
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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