Hydrochloric Acid → HCID 57236764, compound

HRID 581226Notes

Reaction equation

HRID 581226 reaction equation
[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[NH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[CH2:23][C@H:22]([OH:24])[C@@H:21]([CH2:25][OH:26])[CH2:20]2)=[C:12](Cl)[N:11]=1.Cl>>[NH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[CH2:23][C@H:22]([OH:24])[C@@H:21]([CH2:25][OH:26])[CH2:20]2)=[C:12]([O:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)[N:11]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 11108834HCID 11108834, compound

Product 1

HCID 57236764HCID 57236764, compound

Procedure

Sodium hydride (60% oil dispersion, 113 mg was added to cyclopentanol (7 mL). To the resulting solution, after effervescence had ceased, was added (+)-(1S-2R-4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (400 mg, 1.4 mmol). The solution was maintained at 85° for 40 minutes, cooled to room temperature, and neutralized with 1N hydrochloric acid. Volatiles were removed and the residue chromatographed on silica gel. Title compound was eluted with methanol:chloroform/15:85 as a white solid foam which solidified form acetonitrile:methanol/20:1 as a white powder (223 mg, 48%), m.p. 181-182°; mass spectrum (Cl, CH4): 334(M+1); 1H-NMR (DMSO-d6)δ: 7.97 (s, 1, H8), 6.32 (br s, 2, NH2), 5.60 (m, 1, CHO of cyclopentyl) 5.0-4.8 (m, 1, CHN), 4.78 (d, J=4.1 Hz, 1, OH), 4.66 (t, J=5.1 Hz, 1, CH2OH), 4.1 (m, 1, CHOH), 3.6-3.4 (m, 2, CH2O), 2.4-1.9 (m, 6 methylene), 1.9-1.5 (m, 7, methylene); [α]20589 +9.34°, [α]20578 +9.85°, [α]20546 +11.1°, [α]20430 +18.2°, [α]20365 +26.6° (c=0.782, methanol).

Workup

  1. temperatureThe solution was maintained at 85° for 40 minutes
  2. customVolatiles were removed
  3. customthe residue chromatographed on silica gel
  4. washTitle compound was eluted with methanol
  5. custom[α]20589 +9.34°, [α]20578 +9.85°, [α]20546 +11.1°, [α]20430 +18.2°, [α]20365 +26.6° (c=0.782, methanol)

Sources & evidence

ORD record
ord-5653c52302dd495e81b35b6b5c14450d
Source dataset
uspto-grants-1999_07
Patent number
US05919941

Reaction notes

Loading…