5-(4-Tert-butylphenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide → 2-(4-Tert-butylphenyl)-3-hydroxy-3-methylbutane-2-sulfonamide
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:33])[C:16]([CH3:18])([CH3:17])[O:15]C(N[C@H](C3C=CC=CC=3F)CCO)=[N:13][S:12]2(=[O:32])=[O:31])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(C2(C)C(C)(C)OC(OC)=NS2(=O)=O)=CC=1)(C)(C)C.BrC1C=C(C2(C)C(C)(C)OC(N[C@H](C3C=CC=CC=3)CCO)=NS2(=O)=O)C=CC=1>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([S:12]([NH2:13])(=[O:31])=[O:32])([C:16]([OH:15])([CH3:17])[CH3:18])[CH3:33])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]Participants
4
Procedure
The further conversion to (S)-3-[5-(4-tert-butylphenyl)-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-2-ylamino]-3-(2-fluorophenyl)propan-1-ol was effected via the 5-(4-tert-butylphenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide intermediate in analogy to the preparation of (S)-3-[5-(3-bromophenyl)-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-2-ylamino]-3-phenylpropan-1-ol.
Sources & evidence
- ORD record
- ord-2c9a85e53bd34a77b6d8e457cf9db90a
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895547B2
Reaction notes
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