Methyl N-(triethylammoniosulfonyl)carbamate → (S)-4'-(2-(4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-2-cyanoethyl)biphenyl-4-yl methanesulfonate

HRID 216919Notes

Reaction equation

HRID 216919 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([NH:23][C:24]([C:26]3([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[C:20]([NH2:22])=O)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][C@H:19]([NH:23][C:24]([C:26]3([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[C:20]#[N:22])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568621(S)-4'-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-4-yl methanesulfonate

Product 1

HCID 59568586(S)-4'-(2-(4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-2-cyanoethyl)biphenyl-4-yl methanesulfonateYield 117.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4′-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-4-yl methanesulfonate (Example 6, step (i), 234 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (199 mg) and the mixture was stirred at room temperature for 18 h. It was partially evaporated and then purified by chromatography on silica using diethyl ether and then 1:1 ethyl acetate/isohexane as eluent to a afford the sub-titled compound as a white solid (267 mg).

Workup

  1. customIt was partially evaporated
  2. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-d41edf7901e84abf88064f54e6492c69
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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