Pyridine → 3-(Tert-butoxycarbonyl)-4-(3-bromophenyl)-4-methyl[1,2,3]-oxathiazolidine-2-oxide

HRID 1927166Notes

Reaction equation

HRID 1927166 reaction equation
[O:1]=[S:2](Cl)Cl.[Br:5][C:6]1[CH:7]=[C:8]([C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:15])[CH2:13][OH:14])[CH:9]=[CH:10][CH:11]=1.N1C=CC=CC=1>CC#N>[C:19]([O:18][C:17]([N:16]1[C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([Br:5])[CH:7]=2)([CH3:15])[CH2:13][O:14][S:2]1=[O:1])=[O:23])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 57514173HCID 57514173, compound

Product 1

HCID 673041463-(Tert-butoxycarbonyl)-4-(3-bromophenyl)-4-methyl[1,2,3]-oxathiazolidine-2-oxideYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of SOCl2 (5.7 mL, 2.5 eq) in dry CH3CN (37 mL) under argon was cooled to −40° C. was added tert-butyl 2-(3-bromophenyl)-1-hydroxypropan-2-ylcarbamate (DC3; R4=Me) (10.3 g, 31 mmol) in dry CH3CN (27 mL) was added dropwise, followed by the addition of dry pyridine (12.4 mL, 160 mmol, 5 eq). The mixture was then allowed to warm to RT in 1 h. The mixture was concentrated to about 30 mL. EtOAc (30 mL) was added and the precipitate was filtered off. The filtrate was concentrated in vacuo to give 10.4 g (89%) of 3-(tert-butoxycarbonyl)-4-(3-bromophenyl)-4-methyl-[1,2,3]-oxathiazolidine-2-oxide as a colorless oil. 1H NMR (CDCl3) 7.64 (t, J=2.0 Hz, 1H), 7.36-7.53 (m, 2H), 7.24 (m, 1H), 4.52 (q, J=9.5 Hz, 2H), 1.86 (s, 3H), 1.42 (br s, 9H).

Workup

  1. additionwas added dropwise
  2. concentrationThe mixture was concentrated to about 30 mL
  3. additionEtOAc (30 mL) was added
  4. filtrationthe precipitate was filtered off
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8545d27f996c49b688a775d5d856e19c
Source dataset
uspto-grants-2012_05
Patent number
US08183252B2

Reaction notes

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