N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester → N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine

HRID 77319Notes

Reaction equation

HRID 77319 reaction equation
C([O:5][C:6](=[O:31])[C@@H:7]([CH:28]([CH3:30])[CH3:29])[N:8]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])(C)(C)C>Cl.C(OCC)(=O)C>[CH2:23]([N:8]([S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])[C@@H:7]([C:6]([OH:31])=[O:5])[CH:28]([CH3:30])[CH3:29])[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

4

Reactant 1

HCID 67155390N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

Product 1

HCID 67155085N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valineYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (0.33 g, 0.74 mmol) is dissolved in 4 N hydrochloric acid in ethyl acetate (50 mL), and the reaction is allowed to stir at ambient temperature for 16 h. The solvent is removed in vacuo, and the residue is purified by column chromatography (15% hexanes-ethyl acetate) to afford the title compound as a colorless oil (0.26 g, 90% yield). LCMS (m/z): (394.24, M+1; 392.27, M−1).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by column chromatography (15% hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-a3b6b420b2a94a34aed015fcc350f7fa
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Reaction notes

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