Hydrochloric Acid → 2-[[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]amino]-5-[[(phenylmethoxy)carbonyl]amino]pentanoic acid

HRID 6367

Reaction equation

[C:1]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[S:20](Cl)([C:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:28]([N:29]([CH3:31])[CH3:30])[C:27]=2[CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21].Cl>[OH-].[Na+].O1CCCC1>[CH3:30][N:29]([CH3:31])[C:28]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:27]=1[CH:26]=[CH:25][CH:24]=[C:23]2[S:20]([NH:16][CH:15]([CH2:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[C:17]([OH:19])=[O:18])(=[O:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Nδ -Carbobenzyloxy-L-ornithine (39.6 g, 0.149 mol) was dissolved in a solution of 2N NaOH (90 mL) and tetrahydrofuran (200 mL) under nitrogen. After about 15 minutes at ambient temperature, the mixture was cooled to about 0° C. and subsequently treated with additional 2N NaOH (85 mL) and dansyl chloride (45.0 g, 0.167 mol) in 5 g portions over 15 minutes. The mixture was stirred at about 0° C. for about 1 hour and at room temperature for about 2 hours before it was neutralized to pH 7 with 1N HCl. The precipitate was suction-filtered and the filtrate was diluted with ethyl acetate. The organic phase was then separated, washed with brine, dried over Na2SO4 and concentrated to give a combined yield of 103.17 g (70.4%, two runs) of 2d as a yellow foam which was used directly.

Workup

filtrationThe precipitate was suction-filtered
additionthe filtrate was diluted with ethyl acetate
customThe organic phase was then separated
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-d66b4eef54b0430690c4005529ed7d6e
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05248673

Linked notes

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