Hydrochloric Acid → (S)-1-((S)-2-amino-2-phenyl-acetyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester hydrochloride

HRID 1477161Notes

Reaction equation

HRID 1477161 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:15](=[O:31])[C@@H:16]([NH:23]C(OC(C)(C)C)=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])[CH3:2].[ClH:32].O1CCOCC1>>[ClH:32].[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:15](=[O:31])[C@@H:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 117873136HCID 117873136, compound

Product 1

HCID 117871727(S)-1-((S)-2-amino-2-phenyl-acetyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester hydrochloride

Procedure

To (S)-1-((S)-2-tert-butoxycarbonylamino-2-phenyl-acetyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (2.78 g, 6.55 mmol, Eq: 1) was added 4 M HCl in dioxane (16.4 mL, 65.5 mmol, Eq: 10). The mixture was stirred at rt for 2 h. The solvent was removed in vacuo. After drying under vacuum, (S)-1-((S)-2-amino-2-phenyl-acetyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester hydrochloride was obtained as an off-white solid which was used for next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customAfter drying under vacuum

Sources & evidence

ORD record
ord-d25786e5b0e6450f9f414b698ad35b5d
Source dataset
uspto-grants-2016_08
Patent number
US09403768B2

Reaction notes

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