m-Chloroperbenzoic acid → HCID 14654976, compound

HRID 1494514Notes

Reaction equation

HRID 1494514 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([S:19][NH2:20])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[CH2:12]3)[C:6]=2[N:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:26]>CCO>[NH2:1][C:2]1[N:3]=[C:4]([S:19]([NH2:20])=[O:26])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[CH2:12]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14654966HCID 14654966, compound

Product 1

HCID 14654976HCID 14654976, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo[2,3-d1pyrimidine-4-sulfenamide 38 (300 mg, 1 mmol) was suspended in EtOH (120 mL) and cooled to 0° C. m-Chloroperoxybenzoic acid (85%, 100 mg, 1 mmol) in EtOH (30 mL) was added dropwise during 1.5 h. After stirring for an additional 30 min at 0° C., the mixture was concentrated to 10 mL in vacuo below 25° C. Ethyl ether (100 mL) was added to the concentrate solution and allowed to stand in the refrigerator overnight. The precipitate was collected by filtration, washed with ethyl ether and dried at 25° C. under reduced pressure to yield 110 mg (35%) of desired compound 39: m.p. 122 C (dec): UV: λmax (pH 1) 352 nm (ε3,100): 272 (3,100), 240 (21,100): λmax (pH 7 ) 336 nm (ε4,800), 239 (21,500): λmax (pH 11) 337 nm (ε4,600), 239 (20,500): IR (KBr) 1060 (S=O) cm-1 :1H NMR (DMSO-d6): δ6.45 (s, 2, exchangeable in D2O, SONH2), 6.49, (dd, 1, J =8.3 and 5.9 Hz, C1'H), 6.62 (s, 2, exchangeable in D2O, NH2), 6.73 (d, 1, J 3.8 Hz, C5H), 7.38 (d, 1, J =3.8 Hz, C6H). Anal. Calcd for C11H15N5O4S: C, 42.16: H, 4.82: N, 22.35: S, 10.23. Found: C, 41.91: H, 4.86: N, 22.07: S, 9.91.

Workup

  1. additionwas added dropwise during 1.5 h
  2. concentrationthe mixture was concentrated to 10 mL in vacuo below 25° C
  3. additionEthyl ether (100 mL) was added to the concentrate solution
  4. customto stand in the refrigerator overnight
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ethyl ether
  7. customdried at 25° C. under reduced pressure

Sources & evidence

ORD record
ord-50c8a37b23884b818c3694d5c39211ba
Source dataset
uspto-grants-1991_06
Patent number
US05026836

Reaction notes

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