Citric Acid → HCID 118574197, compound

HRID 1055472Notes

Reaction equation

HRID 1055472 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([N:10]([CH3:50])[C@@H:11]([CH3:49])[C:12]([NH:14][C@H:15]1[C@H:21]([CH3:22])[O:20][C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[N:17]([CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]([C:37]3[CH:45]=[CH:44][C:40]([C:41]([O-:43])=[O:42])=[CH:39][C:38]=3[C:46]#[N:47])[N:29]=2)[C:16]1=[O:48])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:3]([O:7][C:8]([N:10]([CH3:50])[C@@H:11]([CH3:49])[C:12]([NH:14][C@H:15]1[C@H:21]([CH3:22])[O:20][C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[N:17]([CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]([C:37]3[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][C:38]=3[C:46]#[N:47])[N:29]=2)[C:16]1=[O:48])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 131736371HCID 131736371, compound

Product 1

HCID 118574197HCID 118574197, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1 N, 448 μl, 448 μmol, Eq: 1.3) was added to a solution of 4-(3-(((2S,3S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-methyl-4-oxo-3,4-dihydrobenzo[b][1,4]oxazepin-5(2H)-yl)methyl)-1H-indazol-1-yl)-3-cyanobenzoate (230 mg, 345 μmol, Eq: 1.00) in THF (7 mL) at 0° C. and H2O (3 mL) was added. After 7 h the mixture was acidified with citric acid to pH 4-5 and was extracted with EtOAc. The combined extracts were washed with H2O, dried over Na2SO4 and concentrated to give 4-(3-(((2S,3S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-methyl-4-oxo-3,4-dihydrobenzo[b][1,4]oxazepin-5(2H)-yl)methyl)-1H-indazol-1-yl)-3-cyanobenzoic acid (220 mg, 97.7%) which was used without purification.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe combined extracts were washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-defbccd28f7c476a9b910c6937e5bfeb
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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