Methanol → HCID 131713679, compound

HRID 2417869Notes

Reaction equation

HRID 2417869 reaction equation
[C:1]([NH:9][C@@H:10]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:11](=[O:30])[CH2:12][NH:13][C@H:14]([C:16]([N:18]1[CH2:29][CH2:28][CH2:27][C@H:19]1[C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:38].N1CCC[C@H]1C(O)=O.CO.C(O)CCC.C(O)(=O)C.O>Cl.C(O)(=O)C>[ClH:38].[C:1]([NH:9][C@@H:10]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:11](=[O:30])[CH2:12][NH:13][C@H:14]([C:16]([N:18]1[CH2:29][CH2:28][CH2:27][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10285808Proline hydrochloride, L-HCID 141273661-[N-[(S)-3-(Benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, 1,1-dimethylethyl esterHCID 22056973Butanol acetic acid water

Product 1

HCID 131713679HCID 131713679, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

1-[N-[(S)-3-(Benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, 1,1-dimethylethyl ester (740 mg., 1.46 mmole) is dissolved in a solution of hydrogen chloride in acetic acid (1.5N, 10 ml.) and kept at room temperature for 30 minutes. It is then concentrated, taken into water, filtered and lyophilized to obtain 600 mg. of 1-[N-(S)-3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanyl]-L-proline, monohydrochloride; m.p. 83°-163°; [α]D25 =-109° (c=1.04, methanol). Rf 0.6 (silica gel; butanol/acetic acid/water, 4:1:1).

Workup

  1. concentrationIt is then concentrated
  2. filtrationfiltered
  3. customto obtain 600 mg

Sources & evidence

ORD record
ord-e781ce666f694b0e807b6a031d7eb85e
Source dataset
uspto-grants-1984_09
Patent number
US04470973

Reaction notes

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