Water → HCID 136347172, compound

HRID 601355Notes

Reaction equation

HRID 601355 reaction equation
[NH2:1][C:2]1[C:11]2[S:10](=[O:13])(=[O:12])[N:9]=[C:8]([C:14]3[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]4[C:22]([C:23]=3[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=4)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:31].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(C(C)C)CC)(C)C.O>O1CCCC1>[CH3:32][S:33]([O:31][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]([C:14]3[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]4[C:22]([C:23]=3[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:9][S:10](=[O:12])(=[O:13])[C:11]=2[C:2]=1[NH2:1])(=[O:35])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 136358419HCID 136358419, compound

Product 1

HCID 136347172HCID 136347172, compoundYield 247.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 354 (44 mg, 0.099 mmol) and methane sulfonyl chloride (0.010 mL, 0.011 mmol) in tetrahydrofuran (4 mL) was treated with diisopropylethylamine (0.075 mL, 0.040 mmol) at roo, temperature for 2 hours. The solution was poured into water. The resulting the precipitate was filtered, dried, and purified by flash column, eluting with 1% methanol in dichloromethane to yield the title compound (14.2 mg, 28%). The sodium salt was made by the procedure of Example 1D. MS (ESI−) m/z 520 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.03 (d, J=6.62 Hz, 6 H) 1.88 (m, 1 H) 2.71 (m, 2 H) 3.46 (s, 3 H) 5.94 (m, 1 H) 6.53 (m, 1 H) 7.16 (m, 1 H) 7.35 (m, 1 H) 7.64 (m, 2 H) 8.09 (d, J=7.35 Hz, 1 H) 16.23 (s, 1 H).

Workup

  1. filtrationThe resulting the precipitate was filtered
  2. customdried
  3. custompurified by flash column
  4. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-cddff2e8da1e4754a37faf88323b909e
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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