Hydrochloric Acid → HCID 68800096, compound

HRID 2222992Notes

Reaction equation

HRID 2222992 reaction equation
C([O:3][C:4](=[O:31])[C@@H:5]([NH:13][C:14](=[O:30])[CH:15]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.O1CCCC1.O.O.[OH-].[Li+].Cl>[Cl-].[Na+].O.O>[C:26]([O:25][C:23]([NH:22][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:14]([NH:13][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:4]([OH:31])=[O:3])=[O:30])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 68802560HCID 68802560, compound

Product 1

HCID 68800096HCID 68800096, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-(S)-(2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-phenyl-propionic acid ethyl ester (≈20 mmol) in 3:1 v/v tetrahydrofuran/water (80 mL total) was added lithium hydroxide monohydrate (1.06 g, 25.3 mmol) and the mixture was stirred at ambient temperature for 5 hours. The reaction mixture was poured into water (300 mL), diluted with brine (100 mL), acidified with 1M aqueous hydrochloric acid (30 mL, 30 mmol) and extracted with ethyl acetate (3×100 mL). the combined organic extracts were washed with brine (2×100 mL), dried with sodium sulfate and concentrated in vacuo to give 2-(S)-(2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-phenyl-propionic acid as a colorless solid (8.16 g, 100%).

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washthe combined organic extracts were washed with brine (2×100 mL)
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2231024a267f4e239ff002b2f0f2111d
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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