Water → 4-Chloro-2-[isobutoxycarbonyl-(2-pyrrolidin-1-yl-ethyl)-amino]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

HRID 1172488Notes

Reaction equation

HRID 1172488 reaction equation
[CH2:1]([O:5][C:6](Cl)=[O:7])[CH:2]([CH3:4])[CH3:3].C[O:10][C:11]([C:13]1[CH:14]=[C:15]([CH3:39])[C:16]2[O:22][C:21]3[C:23]([Cl:35])=[CH:24][C:25]([NH:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:26][C:20]=3[CH2:19][S:18](=[O:37])(=[O:36])[C:17]=2[CH:38]=1)=[O:12].C(N(CC)CC)C.O>C(Cl)Cl>[Cl:35][C:23]1[C:21]2[O:22][C:16]3[C:15]([CH3:39])=[CH:14][C:13]([C:11]([OH:12])=[O:10])=[CH:38][C:17]=3[S:18](=[O:37])(=[O:36])[CH2:19][C:20]=2[CH:26]=[C:25]([N:27]([C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1317284574-Chloro-6-methyl-10,10-dioxo-2-(2-pyrrolidin-1-yl-ethylamino)-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284594-Chloro-2-[isobutoxycarbonyl-(2-pyrrolidin-1-yl-ethyl)-amino]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Isobutylchloroformate (0.17 mL, 1.33 mmol) was added to a solution of Example 72k (0.40 g, 0.88 mmol) in dry CH2Cl2 (15 mL). Triethylamine (0.23 ml, 1.67 mmol) was added and the reaction mixture was stirred at 0° C. for 1 h. It was brought to room temperature, treated with water and extracted with chloroform. The organic layer was washed with water, brine, dried, concentrated and crystallised using ethyl acetate to obtain the title compound as a white solid. Yield: 0.280 g, (58%). 1H NMR (DMSO-d6): δ 0.80 (d, 6H, 2CH3), 1.70-1.80 (m, 5H, 2CH2, CH), 2.50-2.89 (m, 1H, 4CH2, CH3), 3.90 (d, 2H, CH2), 5.19 (s, 2H, CH2), 7.55 (s, 1H, Ar), 7.75 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.20 (s, 1H, Ar). MS: m/e (EI+) 565 (M+).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customcrystallised

Sources & evidence

ORD record
ord-0df1b14e9bac447aa91dd01811181616
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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