Phosphoric Acid → (S)-N-((S)-5-((1-Ethyl-2-oxoindolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamide

HRID 1055463Notes

Reaction equation

HRID 1055463 reaction equation
P(=O)(O)(O)[OH:2].Cl[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][N:17]2[C:23](=[O:24])[C@@H:22]([NH:25][C:26](=[O:38])[C@@H:27]([N:29](C)[C:30](=O)OC(C)(C)C)[CH3:28])[CH2:21][O:20][C:19]3[CH:39]=[CH:40][CH:41]=[CH:42][C:18]2=3)[N:9]([CH2:43][CH3:44])[CH:8]=1>C([O-])(O)=O.[Na+]>[CH2:43]([N:9]1[C:10]2[C:15](=[C:14]([CH2:16][N:17]3[C:23](=[O:24])[C@@H:22]([NH:25][C:26](=[O:38])[C@@H:27]([NH:29][CH3:30])[CH3:28])[CH2:21][O:20][C:19]4[CH:39]=[CH:40][CH:41]=[CH:42][C:18]3=4)[CH:13]=[CH:12][CH:11]=2)[CH2:7][C:8]1=[O:2])[CH3:44]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 131736364tert-butyl (S)-1-((S)-5-((3-chloro-1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Product 1

HCID 73055432(S)-N-((S)-5-((1-Ethyl-2-oxoindolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamideYield 14.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Phosphoric acid (13.2 mg, 2 mL, 108 μmol, Eq: 1.00) was added to tert-butyl (S)-1-((S)-5-((3-chloro-1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (60 mg, 108 μmol, Eq: 1.00) and the mixture stirred at RT for 2 h. The mixture was diluted with sat. NaHCO3 and extracted with DCM. The combined extracts were concentrated and the residue was purified by preparative TLC to give the title compound (7 mg, 14%) as a solid. MS m/z 437 (MH+)

Workup

  1. extractionextracted with DCM
  2. concentrationThe combined extracts were concentrated
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-a13f11537ddb45eab2030ebe71f9a716
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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