Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4-(1-methyl-2-oxoindolin-6-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216951Notes

Reaction equation

HRID 216951 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:22][C:23]([C:25]1([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[C:18]3[C:14]([CH2:15][C:16](=[O:21])[N:17]3[CH3:20])=[CH:13][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:22][C:23]([C:25]1([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[C:18]3[C:14]([CH2:15][C:16](=[O:21])[N:17]3[CH3:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568615(S)-tert-Butyl 4-(1-amino-3-(4-(1-methyl-2-oxoindolin-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568567(S)-tert-Butyl 4-(1-cyano-2-(4-(1-methyl-2-oxoindolin-6-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-tert-butyl 4-(1-amino-3-(4-(1-methyl-2-oxoindolin-6-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 21, step (i), 44 mg) in dichloromethane (5 mL) was treated with Burgess' reagent (25 mg) and stirred at room temperature for 24 h. The reaction was diluted with dichloromethane (50 mL) and washed with water (50 mL). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to the sub-titled compound (35 mg).

Workup

  1. washwashed with water (50 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated in vacuo to the sub-titled compound (35 mg)

Sources & evidence

ORD record
ord-ba6ac62e435047aab144e8e2d20a3316
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

Loading…