Water → HCID 58019871, compound

HRID 1632097Notes

Reaction equation

HRID 1632097 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[OH:8][C@@H:9]1[CH2:13][N:12]([CH2:14][C:15]2[CH:16]=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)[C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[C:11](=[O:32])[CH2:10]1.O>ClCCl>[CH3:22][O:21][C:18]1[C:17]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)=[CH:16][C:15]([CH2:14][N:12]2[C:11](=[O:32])[CH2:10][C@H:9]([O:8][C:6](=[O:7])[NH2:5])[CH2:13]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 58020098HCID 58020098, compound

Product 1

HCID 58019871HCID 58019871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 20 mL vial with a stir bar was added chlorosulfonyl isocyanate (42 mg, 0.30 mmol), 1 mL dichloromethane, then P-248 (51.3 mg, 0.15 mmol) in 2 mL of dichloromethane. The reaction was stirred at room temperature for 18 hours after which 2 mL of water was added and the mixture was stirred at room temperature for 30 minutes. The layers were separated and the aqueous was extracted with dichloromethane. The combined organics were concentrated and then purified by preparative layer TLC using 50% acetone/dichloromethane to obtain P-253 (12.4 mg, 21%) as an off-white semi-solid. 1H NMR (400 MHz, DMSO-d6) 8.30 (s, 1H), 8.20 (dd, J=2.1, 8.6 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 7.72 (t, J=8.0 Hz, 1H), 7.33-7.26 (m, 2H), 7.16 (d, J=9.0 Hz, 1H), 6.59 (br. s., 2H), 5.04 (t, J=5.8 Hz, 1H), 4.49-4.30 (m, 2H), 3.80 (s, 3H), 3.46-3.38 (m, 1H), 3.21 (d, J=11.4 Hz, 1H), 2.78 (dd, J=6.9, 17.5 Hz, 1H), 2.23 (d, J=18.1 Hz, 1H) ppm. LC/MS=100.0%, 386.1 (APCI+).

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with dichloromethane
  4. concentrationThe combined organics were concentrated
  5. custompurified by preparative layer TLC
  6. customto obtain P-253 (12.4 mg, 21%) as an off-white semi-solid

Sources & evidence

ORD record
ord-9997a8c677eb4301ba1541d4d5b857f5
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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