Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4-iodophenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216938Notes

Reaction equation

HRID 216938 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:2]([C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568614(S)-tert-Butyl 4-(1-cyano-2-(4-iodophenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 0.610 g) in dichloromethane (15 mL) was treated with Burgess' reagent (0.365 g) and the mixture was stirred at room temperature for 2 days. The reaction mixture was absorbed onto silica and purified by chromatography on silica eluting with 25% ethyl acetate in isohexane, then 50% ethyl acetate in isohexane to afford the sub-titled compounds (0.402 g) as white crystals.

Workup

  1. customThe reaction mixture was absorbed onto silica
  2. custompurified by chromatography on silica eluting with 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-54938e7cd33f4172bf62d7878d53d41e
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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