Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(3'-(methylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216957Notes

Reaction equation

HRID 216957 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:21][C:22]([C:24]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[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:21][C:22]([C:24]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=2)=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568587(S)-tert-Butyl 4-(1-amino-3-(3'-(methylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568565(S)-tert-Butyl 4-(1-cyano-2-(3'-(methylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(3′-(methylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 23, step (i), 320 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (280 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and the mixture was purified by chromatography on silica eluting with 1:1 ethyl acetate/isohexane as eluent to afford the sub-titled compound (230 mg).

Workup

  1. customThe solvent was partially evaporated
  2. customthe mixture was purified by chromatography on silica eluting with 1:1 ethyl acetate/isohexane as eluent

Sources & evidence

ORD record
ord-8a13e11c01aa46c595a6a49126ad0636
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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