Hydrochloric Acid → HCID 60202699, compound

HRID 1952663Notes

Reaction equation

HRID 1952663 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:26](=[O:38])[NH:27][CH2:28][C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][NH:33]3)=[CH:20][C:21]=1[C:22]([F:25])([F:24])[F:23])=[O:16])[CH2:5][NH:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8].O.[OH-].[Li+].Cl>C1COCC1.O>[NH:33]1[C:34]2[C:30](=[C:29]([CH2:28][NH:27][C:26]([C:19]3[S:18][C:17]([C:15]([NH:14][C@@H:4]([CH2:5][NH:6][C:7]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[O:8])[C:3]([OH:39])=[O:2])=[O:16])=[C:21]([C:22]([F:23])([F:25])[F:24])[CH:20]=3)=[O:38])[CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:32]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226934HCID 68226934, compound

Product 1

HCID 60202699HCID 60202699, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-({5-[(1H-Indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carbonyl}-amino)-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (170 mg, 0.29 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (120 mg, 2.94 mmol) in water (8 mL). The mixture was then stirred at room temperature overnight. The mixture was then acidified with 1N HCl and extracted with EtOAc (×3). The extracts were combined, washed with water and brine, dried over sodium sulfate, filtered, and evaporated to pure product, 0.1089 g (67%). MS m/e 564.9 (M+H+).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to pure product, 0.1089 g (67%)

Sources & evidence

ORD record
ord-9c449b8bb65141f481d57c24a1c1c8a6
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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