Dichloromethane → HCID 86757643, compound

HRID 2268400Notes

Reaction equation

HRID 2268400 reaction equation
[OH:1][C@@H:2]([C@H:6]([OH:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[C:11]1([CH:17]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:18][NH:19][C:20]2[N:28]=[C:27]([CH2:29][NH:30][CH:31]3[CH2:36][CH2:35][N:34]([CH:37]([CH3:39])[CH3:38])[CH2:33][CH2:32]3)[N:26]=[C:25]3[C:21]=2[N:22]=[CH:23][N:24]3[C@H:40]2[C@H:44]([OH:45])[C@H:43]([OH:46])[C@@H:42]([CH2:47][O:48][CH3:49])[O:41]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.ClCCl>C(O)(C)C>[OH:1][C@@H:2]([C@H:6]([OH:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[C:11]1([CH:17]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:18][NH:19][C:20]2[N:28]=[C:27]([CH2:29][NH:30][CH:31]3[CH2:36][CH2:35][N:34]([CH:37]([CH3:38])[CH3:39])[CH2:33][CH2:32]3)[N:26]=[C:25]3[C:21]=2[N:22]=[CH:23][N:24]3[C@H:40]2[C@H:44]([OH:45])[C@H:43]([OH:46])[C@@H:42]([CH2:47][O:48][CH3:49])[O:41]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 439655D-Tartaric acidHCID 9895232HCID 9895232, compound

Product 1

HCID 86757643HCID 86757643, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent4×

Procedure

A solution of (2S,3S)-2,3-dihydroxybutanedioic acid (49 mg, 0.33 mmol) in isopropyl alcohol (1 ml) was added to a stirred solution of [((2R,3R,4S,5R)-2-(6-[(2,2-diphenylethyl)amino]-2-{[(1-isopropyl-4-piperidinyl)amino]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol (200 mg, 0.33 mmol) (example 16) in isopropyl alcohol (1 ml). This resulted in the formation of a thick precipitate, which was dissolved by the addition of dichloromethane and isopropyl alcohol. The solvent was boiled off from the solution until a gum started to appear and then more isopropyl alcohol was added. The resulting white crystalline solid was filtered off, dried and then recrystallized from hot ethanol to give the title compound (40 mg) as a white powder. M.p. 161-163° C.

Workup

  1. customThis resulted in the formation of a thick precipitate, which
  2. filtrationThe resulting white crystalline solid was filtered off
  3. customdried
  4. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-a4b353ba813e4c70907cc1587aaacb3f
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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