Hydrochloric Acid → (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid

HRID 724709Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11].[OH-].[Na+].Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].Cl>O1CCCC1.O>[CH2:34]([O:33][C:31]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:18][CH:19]=1)[C:10]([OH:12])=[O:11])=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid trifluoroacetate (45 mg, 109 μmol), sodium hydroxide (26.2 mg, 655 μmol), water (100 μL) and tetrahydrofuran (2 mL) was cooled to 0° C. and then benzyl chloroformate (18.7 μL, 131 μmol) was added. The reaction was warmed to 25° C. and stirred for 20 h. The solution was acidified with 1 N aq. HCl solution (1.00 mL) and the crude residue was purified by preparative LCMS to yield the desired product (13 mg, 28%). MF=C20H20N2O7S; LCMS found for C20H21N2O7S (M+H)+: m/z=433.

Workup

customthe crude residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-13d345ca4d3c4d18861a693256b12d0e
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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