Hydrochloric Acid → diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate hydrochloride

HRID 2230400Notes

Reaction equation

HRID 2230400 reaction equation
[OH:1][C@@H:2]([C@H:30]([OH:45])[C@H:31]([OH:44])[C@@H:32]([NH:35][C:36](=[O:43])[C@H:37]([CH2:39][CH:40]([CH3:42])[CH3:41])[NH2:38])[CH2:33][OH:34])[C:3]([NH:5][C@H:6]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:7][C:8]([O:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:4].[ClH:46]>CO>[ClH:46].[OH:1][C@@H:2]([C@H:30]([OH:45])[C@H:31]([OH:44])[C@@H:32]([NH:35][C:36](=[O:43])[C@H:37]([CH2:39][CH:40]([CH3:41])[CH3:42])[NH2:38])[CH2:33][OH:34])[C:3]([NH:5][C@H:6]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:7][C:8]([O:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11039599diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

Product 1

HCID 86758377diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate (246 mg) in methanol (1 ml) was added 1N hydrochloric acid (0.396 ml) at room temperature. Concentration gave a residue, which was recrystallized from methanol-diethylether to afford the title compound (180 mg).

Workup

  1. concentrationConcentration
  2. customgave a residue, which
  3. customwas recrystallized from methanol-diethylether

Sources & evidence

ORD record
ord-a5f371af95b54eae88955f2c09e6e645
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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