Chlorosulfamic acid → (1S,2R,3R,5R)-3-{[(Aminosulfonyl)oxy]methyl}-5-(isonicotinoylamino)cyclopentane-1,2-diyl dibenzoate

HRID 1677938Notes

Reaction equation

HRID 1677938 reaction equation
[C:1]([O:9][C@H:10]1[C@H:14]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:13][C@H:12]([CH2:24][OH:25])[C@H:11]1[O:26][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.Cl[S:47]([NH2:50])(=[O:49])=[O:48]>C(#N)C>[C:1]([O:9][C@H:10]1[C@H:14]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:13][C@H:12]([CH2:24][O:25][S:47]([NH2:50])(=[O:49])=[O:48])[C@H:11]1[O:26][C:27](=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66797861(1S,2R,3R,5R)-3-(Hydroxymethyl)-5(isonicotinoylamino)cyclopentane-1,2-diyl dibenzoate

Product 1

HCID 86618707(1S,2R,3R,5R)-3-{[(Aminosulfonyl)oxy]methyl}-5-(isonicotinoylamino)cyclopentane-1,2-diyl dibenzoateYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (1S,2R,3R,5R)-3-(hydroxymethyl)-5-(isonicotinoylamino)cyclopentane-1,2-diyl dibenzoate (160. mg, 0.350 mmol) in ACN (10.0 mL) at 0° C. was added DBU (0.0600 mL, 0.401 mmol) and the mixture was stirred for 15 min. A freshly prepared 1.40 M solution of chlorosulfonamide (0.500 mL, 0.700 mmol, as prepared in Example 1d) was then added dropwise via syringe and the mixture was stirred for 2.5 h at 0° C. before being allowed to warm to rt. The mixture was concentrated in vacuo and the residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in E)CM to afford the title compound (50.0 mg, 27%). LC/MS: Rt=1.57 min, ES+ 540. (FA standard).

Workup

  1. stirringthe mixture was stirred for 2.5 h at 0° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified via silica gel chromatography
  4. washeluting with a gradient of 0 to 10% MeOH in E)CM

Sources & evidence

ORD record
ord-e22387c3a4a044fd8f15f74b8f6aead2
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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