Hydrochloric Acid → HCID 69800351, compound

HRID 488659Notes

Reaction equation

HRID 488659 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:35]=[CH:34][C:14]([CH2:15][C@@H:16]([C:25]([O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=[O:26])[NH:17]C(OC(C)(C)C)=O)=[CH:13][CH:12]=1)([OH:3])=[O:2].Cl.O1CCOCC1>>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:35]=[CH:34][C:14]([CH2:15][C@@H:16]([C:25]([O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:31])[CH3:33])=[O:26])[NH2:17])=[CH:13][CH:12]=1)([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69800441HCID 69800441, compound

Product 1

HCID 69800351HCID 69800351, compoundYield 109.6%

Procedure

2-(trimethylsilyl)ethyl 4-[(2-carboxyphenyl)amino]-N-(tert-butoxycarbonyl)-L-phenylalaninate (6.97 g, 13.9 mmol) was treated with 4N HCl (13.9 mL) in Dioxane (55.8 mmol) for one hour. The solvent was then removed under reduced pressure. The residue was precipitated with diethyl ether (2×35 mL) to provide the titled compound as a light yellow solid (6.1 g, 100%).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customThe residue was precipitated with diethyl ether (2×35 mL)

Sources & evidence

ORD record
ord-28586efd0f51453a9d427b1625b62724
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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