1,3-Dithiane, 1,1,3,3-tetraoxide → HCID 22852345, compound
Reaction equation
N[C@@H:2]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C@@H:3](O)[CH2:4][CH2:5][CH:6]1[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][CH2:8][S:7]1(=[O:15])=[O:14].N[C@@H:25](CC1CCCCC1)[C@@H](O)CCCC1S(=O)(=O)CCCS1(=O)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[C:62]([N:69]1[C@@](C)(C2CCCCC2)[C@H](CCOS(C)(=O)=O)[O:71][C:70]1([CH3:89])[CH3:88])([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63].S1(=O)(=O)CCCS(=O)(=O)C1>>[C:62]([N:69]1[C@@H:17]([CH2:18][CH:23]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:25]2)[C@H:2]([CH2:3][CH2:4][CH2:5][CH:6]2[S:7](=[O:14])(=[O:15])[CH2:8][CH2:9][CH2:10][S:11]2(=[O:12])=[O:13])[O:71][C:70]1([CH3:88])[CH3:89])([O:64][C:65]([CH3:66])([CH3:67])[CH3:68])=[O:63]Participants
Procedure
In analogy to Example 3, there are obtained from2-[(2S,3S)-3-amino-4-cyclohexyl-2-hydroxy-butyl]-1,3-dithiane 1, 1,3,3-tetroxide or from 2-[(3S, 4S)-4-amino-5-cyclohexyl-3-hydroxypentyl]-1,3-dithiane 1,1,3,3-tetroxide or from 2-[(4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-hexyl ]-1,3-dithiane 1,1,3,3-tetroxide [dihydrochloride, m.p. 209°-210° , FAB 382, obtainable from (4S,5S)-3-BOC-4-cyclohexyl-methyl-5-(2-methansulfonyloxy-ethyl)-2,2-di-methyl-oxazolidine via the corresponding 5-(2-cyanoethyl)-, 5-(2-carboxyethyl)-(m.p. 190° (decomposition)), 5-(2-methoxy-carbonyl-ethyl)-(oil; FAB 384), 5-(3-hydroxy-propyl)-(m.p. 60°-61°; FAB 356) and 5-(3-methanesulfonyloxy-propyl)-compounds (m.p. 63°-64°, FAB 434), react ion of the last mentioned compound with 1,3-dithiane 1,1,3,3-tetroxide to yield 2-[3-((4S,5S)-3-BOC-4-cyclohexylmethyl-2,2-dimethyl- 5-oxazolidinyl)-propyl]-1,3-dithiane 1,1,3,3-tetroxide (FAB 522) and cleavage with methanolic hydrochloric acid at 25° the following 1,3-dithiane 1,1,3,3-tetroxides:
Workup
- customreact ion of the
Sources & evidence
- ORD record
- ord-d21c605e2ed54f63a0e565d7a4f57e2b
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401722
Reaction notes
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