HCID 68281405, compound → HCID 86702754, compound

HRID 526261Notes

Reaction equation

HRID 526261 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:33]([NH:41]C(OC(C)(C)C)=O)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:13][C:14]([NH:16][C@@H:17]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[C:18]([NH:20][C@@H:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])=[O:19])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.O1CCOCC1>[NH2:41][C@@H:33]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:13][C:14]([NH:16][C@@H:17]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[C:18]([NH:20][C@@H:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])=[O:19])=[O:15]

Participants

4

Reactant 1

HCID 68281405HCID 68281405, compound

Product 1

HCID 86702754HCID 86702754, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl (S)-2-[(2S,3S)-2-((3S,4S)-3-benzyloxycarbonylamino-4-tertbutoxycarbonylamino-5-phenylpentanoylamino)-3-methylpentanoylamino]-3-methylbutanoate (2.76 g; 4.04 mmol) were dissolved in 10 ml of HCl solution in dioxane (4 M) in a flask, and the mixture was stirred at RT for 5 h. Excess HCl was removed using the house vacuum, the solvent was removed in vacuo, and the residue was lyophilised overnight, giving 2.4 g of methyl (S)-2-[(2S,3S)-2-((3S,4S)-4-amino-3-benzyloxycarbonylamino-5-phenylpentanoylamino)-3-methylpentanoylamino]-3-methylbutyrate as a white solid. (Yield 92.2%, content 94%). MS-FAB (M+H+)=569.3 Rf (polar method): 1.67 min.

Workup

  1. customExcess HCl was removed
  2. customthe solvent was removed in vacuo
  3. waitthe residue was lyophilised overnight

Sources & evidence

ORD record
ord-f15b187a6c6645de80b3a5655c9e7ca3
Source dataset
uspto-grants-2016_05
Patent number
US09345742B2

Reaction notes

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