HCID 57507370, compound → HCID 66992216, compound

HRID 556502Notes

Reaction equation

HRID 556502 reaction equation
[CH3:1][O:2][C:3](=[O:52])[CH:4]([NH:18][C:19](=[O:51])[CH2:20][NH:21][C:22](=[O:50])[C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=1[NH:30][C:31]1([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[CH:44]=2)[C:39]2[C:34](=[CH:35][C:36]([Cl:40])=[CH:37][CH:38]=2)[NH:33][C:32]1=[O:41])[CH2:5][CH2:6][CH2:7][CH:8](N)[NH:9]C(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3](=[O:52])[CH:4]([NH:18][C:19](=[O:51])[CH2:20][NH:21][C:22](=[O:50])[C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=1[NH:30][C:31]1([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[CH:44]=2)[C:39]2[C:34](=[CH:35][C:36]([Cl:40])=[CH:37][CH:38]=2)[NH:33][C:32]1=[O:41])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9]

Participants

3

Reactant 1

HCID 57507370HCID 57507370, compound

Product 1

HCID 66992216HCID 66992216, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The rac-(S)-6-Amino-2-(2-{4-bromo-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoylamino}-acetylamino)-6-tert-butoxycarbonylamino-hexanoic acid methyl ester (200 mg, 0.25 mmol) in 5 mL of TFA was stirred at room temperature for 0.5 hour, and concentrated in vacuo. The residue was added by 10 mL of DCM, then rinsed with 20 mL of water. The organic layer was dried over Na2SO4, and concentrated in vacuo, then purified by flash column chromatopgraphy to 146 mg white solid. MS: 704 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was added by 10 mL of DCM
  3. washrinsed with 20 mL of water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column chromatopgraphy to 146 mg white solid

Sources & evidence

ORD record
ord-81a8eaa2ca6a4ca9b8062ab382935e02
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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