Sulfuric Acid → N6-[(Phenylmethoxy)carbonyl]-L-lysine 1,1-dimethylethyl ester

HRID 1982367Notes

Reaction equation

S(=O)(=O)(O)O.[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]([C:23]([OH:25])=[O:24])[NH2:22])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:26][C:27](=[CH2:29])[CH3:28].[OH-].[Na+]>O1CCOCC1>[CH2:6]([O:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]([C:23]([O:25][C:27]([CH3:29])([CH3:28])[CH3:26])=[O:24])[NH2:22])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Into two separate 500 ml hydrogenation vessels each containing 100 ml of dioxane and 9.0 ml (160 mmol) of concentrated sulfuric acid was placed 11.0 gm (39.2 mmol) and 10.6 gm (37.8 mmol) of Nε-benzyloxycarbonyl-L-lysine. The two solutions were cooled to -78° C. and 140 ml of condensed (-78° C.) isobutylene was added to each vessel. The mixtures were then mechanically shaken (Parr shaker) at room temperature for 4 hours (26 psi). The reaction mixtures were combined and poured into 1000 ml (1.0 mol) of an ice cold solution of 1.0N aqueous sodium hydroxide and subsequently extracted three times with ether. The organic portions were combined (ca. 3000 ml), washed once with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give 16.7 gm (64%) of t-butyl Nε-benzyloxycarbonyl-L-lysinate (IV-A) as an oil.

Workup

additionwas added to each vessel
customThe reaction mixtures
extractionsubsequently extracted three times with ether
washwashed once with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0121c7477f08451db42ef01f11d0cda1
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04596791

Reaction notes

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