Ammonia → [(1R,2R,3S,4R)-2,3-dihydroxy-4-(isonicotinoylamino)cyclopentyl]methyl sulfamate

HRID 447600Notes

Reaction equation

HRID 447600 reaction equation
C([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:26]([NH2:29])(=[O:28])=[O:27])[C@H:11]1[O:30]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N.CO>>[S:26](=[O:28])(=[O:27])([O:25][CH2:24][C@H:12]1[CH2:13][C@@H:14]([NH:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)[C@H:10]([OH:9])[C@@H:11]1[OH:30])[NH2:29]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86618707(1S,2R,3R,5R)-3-{[(Aminosulfonyl)oxy]methyl}-5-(isonicotinoylamino)cyclopentane-1,2-diyl dibenzoate

Product 1

HCID 59671362[(1R,2R,3S,4R)-2,3-dihydroxy-4-(isonicotinoylamino)cyclopentyl]methyl sulfamateYield 40.1%

Procedure

A solution of (1S,2R,3R,5R)-3-{[(aminosulfonyl)oxy]methyl}-5-(isonicotinoylamino)cyclopentane-1,2-diyl dibenzoate (61.1 mg, 0.113 mmol) in a 7.00 M solution of ammonia in MeOH (1.50 mL, 10.5 mmol) was stirred for 2 days. The reaction mixture was then concentrated in vacuo and purified via reverse phase C18 preparative HPLC eluting with a gradient of 5 to 70% of 0.1% FA/95% ACN/5% H2O in 0.1% FA/99% H2O/1% ACN over 16 min to afford the title compound (15.0 mg, 40%). 1H NMR (CD3OD, 300 MHz) δ: 8.67 (m, 2H), 7.78 (m, 2H), 4.34-4.32 (m, 1H), 4.19-4.17 (m, 2H), 3.93-3.92 (m, 2H), 2.38-2.31 (m, 1H), 1.76-1.72 (m, 1H), 1.43-1.38 (m, 1H) ppm. LC/MS: Rt=0.76 min, ES+ 332 (FA standard).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified via reverse phase C18 preparative HPLC
  3. washeluting with a gradient of 5 to 70% of 0.1%
  4. customover 16 min

Sources & evidence

ORD record
ord-3d582be5afab447d9eb22ee7a06b9bc8
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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