Hydrochloric Acid → HCID 68227305, compound

HRID 1952676Notes

Reaction equation

HRID 1952676 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]([NH:17][C:18]([C:20]1[S:21][C:22]([C:27](=[O:39])[NH:28][CH2:29][C:30]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:31]=2[CH:32]=[N:33][NH:34]3)=[CH:23][C:24]=1[C:25]#[N:26])=[O:19])[CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:10]([OH:15])[CH:9]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[C:25]([C:24]1[CH:23]=[C:22]([C:27](=[O:39])[NH:28][CH2:29][C:30]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:31]=2[CH:32]=[N:33][NH:34]3)[S:21][C:20]=1[C:18]([NH:17][C@@H:4]([CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([OH:14])[CH:13]=1)[C:3]([OH:40])=[O:2])=[O:19])#[N:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226789HCID 68226789, compound

Product 1

HCID 68227305HCID 68227305, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-({3-Cyano-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carbonyl}-amino)-3-(3,5-dihydroxy-benzoylamino)-propionic acid methyl ester (124.1 mg, 0.22 mmol) in THF (10 mL) was added a solution of lithium hydroxide monohydrate (65 mg, 1.54 mmol) in water (12 mL). The mixture was then stirred at room temperature 1.5 h. 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 afford to pure product, 78.6 mg (65%). MS m/e 549.0 (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
  6. customto afford to pure product, 78.6 mg (65%)

Sources & evidence

ORD record
ord-4620800080624628bbc0da90672e0de9
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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