Triethylamine → 2,2-Dimethyl-propionic acid (R)-2-{[5-(2,2-dimethyl-propionyloxymethyl)-7-nitro-1H-indole-2-carbonyl]-amino}-3-(4-methoxy-benzylsulfanyl)-propyl ester

HRID 1515258Notes

Reaction equation

HRID 1515258 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]([NH:17][C@@H:18]([CH2:27][S:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:16])=[CH:6]2.CCN(CC)CC.[C:45](Cl)(=[O:50])[C:46]([CH3:49])([CH3:48])[CH3:47]>C(Cl)Cl>[CH3:47][C:46]([CH3:49])([CH3:48])[C:45]([O:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]([NH:17][C@@H:18]([CH2:27][S:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:16])=[CH:6]2)=[O:50]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 595431102,2-Dimethyl-propionic acid (R)-2-[(5-hydroxymethyl-7-nitro-1H-indole-2-carbonyl)-amino]-3-(4-methoxy-benzylsulfanyl)-propyl ester

Product 1

HCID 595431032,2-Dimethyl-propionic acid (R)-2-{[5-(2,2-dimethyl-propionyloxymethyl)-7-nitro-1H-indole-2-carbonyl]-amino}-3-(4-methoxy-benzylsulfanyl)-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl-propionic acid (R)-2-[(5-hydroxymethyl-7-nitro-1H-indole-2-carbonyl)-amino]-3-(4-methoxy-benzylsulfanyl)-propyl ester (3.1 g, 6.01 mmol) prepared in Step A of Preparation 41 was dissolved in DCM, to which was added Et3N (1.68 mL, 12.02 mmol). Pivaloyl chloride (0.92 mL, 6.61 mmol) was added thereto, and the mixture was stirred for 12 h at room temperature. After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/1) to give the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/1)

Sources & evidence

ORD record
ord-62dae2df4af34df6bd8344b5ad7ce2ec
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

Loading…