(6R,8S)-7,7-Dichloro-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide → (-)-4-[2-(Hydroxyamino)-2-oxoethyl]-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2h-1,4-benzothiazine-6-carboxylic acid

HRID 1817199Notes

Reaction equation

HRID 1817199 reaction equation
C([O:5][C:6](=O)[CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:18]([O:20]CC)=[O:19])[CH:16]=[CH:17][C:12]=2[S:11][C@H:10]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:9]1=[O:34])(C)(C)C.BrC1C=C(C(OCC)=O)C=CC=1S[C@@H](CCCC1C=CC(OC)=CC=1)C(O)=O.CC1(C)C23[C@@]4([O:79][N:74]4S(=O)(=O)C2)C(Cl)(Cl)[C@H]1CC3>C(OCC)(=O)C>[OH:79][NH:74][C:6](=[O:5])[CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][C:12]=2[S:11][CH:10]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:9]1=[O:34]

Participants

5

Reactant 3

HCID 16212295(6R,8S)-7,7-Dichloro-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxideHCID 57880342Ethyl (2r)-4-(2-tert-butoxy-2-oxoethyl)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2h-1,4-benzothiazine-6-carboxylateHCID 57880345(2S)-2-{[2-bromo-4-(ethoxycarbonyl)phenyl]thio}-5-(4-methoxyphenyl)pentanoic acid

Product 1

HCID 23157951(-)-4-[2-(Hydroxyamino)-2-oxoethyl]-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2h-1,4-benzothiazine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 14 (25% and 90% e.e.) was obtained by the same process as described in Reference Example 14, except for using the compound of Example 8, (+)-(8,8-dichlorocamphorylsulfonyl)oxaziridine and ethyl acetate as solvent. The optical purity was determined by the method described in Example 14.

Sources & evidence

ORD record
ord-eb5614863fbb4c4f91348a7eab09dde3
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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