Hydrochloric Acid → 4-(6-Bromo-pyridin-2-yl)-4-methyl-2-oxo-2lambda*4*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester

HRID 538311Notes

Reaction equation

HRID 538311 reaction equation
[S:1](Cl)(Cl)=[O:2].N1C=CC=CC=1.[C:11]([O:15][C:16](=[O:29])[NH:17][C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=1)([CH3:21])[CH2:19][OH:20])([CH3:14])([CH3:13])[CH3:12].Cl>C(Cl)Cl>[C:11]([O:15][C:16]([N:17]1[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=2)([CH3:21])[CH2:19][O:20][S:1]1=[O:2])=[O:29])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 87687231[1-(6-Bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 1317311634-(6-Bromo-pyridin-2-yl)-4-methyl-2-oxo-2lambda*4*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an at 0° C. precooled solution of thionyl chloride (3.42 ml, 5.57 g, 46.8 mmol) in pyridine (9.46 ml, 9.25 g, 117.0 mmol) was added dropwise a solution of [1-(6-bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester (see Example 1 step d), 7.75 g, 23.4 mmol) in DCM (230 ml). The reaction mixture was allowed to stir for 1 h at rt, then 0.5 N aq. HCl and DCM were added, the phases were separated and the aq. phase was twice reextracted with DCM. The combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated to leave the title compound (mixture of diastereomers) as an orange solid. HPLC RtH4=1.16, 1.20 min (diastereomers); ESIMS: 377, 379 [(M+H)+].

Workup

  1. customat 0° C.
  2. customthe phases were separated
  3. washphases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f32a6f45b8554e19b02a2140ddeb9be7
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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