Water → (7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-N-{[methyl(2-oxoethyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

HRID 1669398Notes

Reaction equation

HRID 1669398 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:38]([NH:40][S:41]([N:44]([CH2:46][CH:47](OC)[O:48]C)[CH3:45])(=[O:43])=[O:42])=[O:39])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][C@H:16]([N:26]([CH3:37])[CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[NH2:29][CH2:28][CH2:27][N:26]([CH3:37])[C@@H:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:38]([NH:40][S:41]([N:44]([CH3:45])[CH2:46][CH:47]=[O:48])(=[O:42])=[O:43])=[O:39])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86627890tert-butyl {2-{[(7R)-14-cyclohexyl-11-[({[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}amino)carbonyl]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl}(methyl)amino]ethyl}carbamate

Product 1

HCID 86627891(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-N-{[methyl(2-oxoethyl)amino]sulfonyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of tert-butyl {2-[{(7R)-14-cyclohexyl-11-[({[(2,2-dimethoxyethyl)-(methyl)amino]sulfonyl}amino)carbonyl]-7,8-dihydro-6H-indolo[1,2-e][1,5]-benzoxazocin-7-yl}(methyl)amino]ethyl}carbamate (0.03 M) in DCM was treated with TFA (100 eq) and water (180 eq) at RT and the resulting mixture stirred vigorously for 3 h at 40° C. The volatiles were removed in vacuo and the residue diluted with Et2O and re-evaporated to drive off excess TFA. The product was used in the subsequent step without further purification. MS (ES+) m/z 582 (M+H)+; 600 (M+H2O+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue diluted with Et2O
  3. customre-evaporated
  4. customThe product was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-22bf35960c2549a5ad800688cbe4c162
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

Loading…