Hydrochloric Acid → HCID 68858858, compound

HRID 1784237Notes

Reaction equation

HRID 1784237 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:26])[C@@H:5]([NH2:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.[NH2:27][C:28]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:29]=1[C:30](O)=[O:31].Cl>CCOC(C)=O>[CH3:2][O:3][C:4](=[O:26])[C@@H:5]([NH:25][C:30](=[O:31])[C:29]1[CH:33]=[C:34]([Cl:37])[CH:35]=[CH:36][C:28]=1[NH2:27])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:19][CH:20]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 124762-Amino-5-chlorobenzoic acidHCID 68863043HCID 68863043, compound

Product 1

HCID 68858858HCID 68858858, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(2-Amino-5-chloro-benzoylamino)-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester (175 mg) was prepared from (S)-2-amino-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester-hydrochloride (214 mg, 0.57 mmol) and 2-amino-5-chloro-benzoic acid (101 mg) as described in Procedure A, except for an adapted work-up. After reaction completion, the reaction mixture was poured onto 5 mL of 1N HCl and 5 mL of EtOAc. The organic layer was washed with 1N HCl, saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The crude material was purified over silica gel (DCM).

Workup

  1. customAfter reaction completion
  2. washThe organic layer was washed with 1N HCl, saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude material was purified over silica gel (DCM)

Sources & evidence

ORD record
ord-6e660cb4b004408b8e9d605c0420d374
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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