Hydrochloric Acid → HCID 59401936, compound

HRID 384610Notes

Reaction equation

HRID 384610 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:38])[C@@H:16]([NH:21][C:22](=[O:37])/[CH:23]=[CH:24]/[C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[N:32]2[CH:36]=[N:35][N:34]=[N:33]2)[CH2:17][C:18](O)=[O:19])=[CH:10][CH:9]=1)=[O:7])(C)(C)C.O.[OH-].[Li+].Cl.[CH2:43]1[CH2:47]OCC1>O>[Cl:31][C:29]1[CH:28]=[CH:27][C:26]([N:32]2[CH:36]=[N:35][N:34]=[N:33]2)=[C:25](/[CH:24]=[CH:23]/[C:22]([NH:21][C@@H:16]([CH2:17][C:18]([N:21]2[CH2:43][CH2:47][N:14]([CH3:11])[CH2:15][CH2:16]2)=[O:19])[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C:6]([OH:5])=[O:7])=[CH:9][CH:10]=2)=[O:38])=[O:37])[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68475116HCID 68475116, compound

Product 1

HCID 59401936HCID 59401936, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S,E)-4-(4-(tert-butoxycarbonyl)phenylamino)-3-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acrylamido)-4-oxobutanoic acid: To a solution of 17A (1.8 g, 3.24 mmol) in THF (16 mL) was added lithium hydroxide monohydrate (0.30 g, 7.14 mmol) in H2O (16 mL). After 1 h, the reaction mixture was acidified to pH 5-6 with 1.0M HCl and extracted with EtOAc (3×40 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to afford the desired product as an off-white solid. LCMS m/z 541 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×40 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1c049decd57045669585471bbb2c6a1a
Source dataset
uspto-grants-2013_02
Patent number
US08367709B2

Reaction notes

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