Acetic Acid → HCID 59975298, compound

HRID 2268393Notes

Reaction equation

HRID 2268393 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:51][O:52][CH:53]1[CH2:58][CH2:57][C:56](=O)[CH2:55][CH2:54]1.C(O)(=O)C>O1CCCC1>[C:25]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23][NH:22][C:5]2[N:4]=[C:3]([CH2:2][NH:1][CH:56]3[CH2:57][CH2:58][CH:53]([O:52][CH3:51])[CH2:54][CH2:55]3)[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5350284-MethoxycyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 59975298HCID 59975298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by a similar method to example 6 using (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (400 mg, 0.78 mmol) (example 1), sodium triacetoxyborohydride (260 mg, 1.23 mmol), 4-methoxycyclohexanone (100 mg, 0.78 mmol) (J. Am. Chem. Soc. 5190, 89, 1967) and acetic acid (56 mg, 0.93 mmol) in tetrahydrofuran (30 ml). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (94:6:0.3) to give the title compound as a mixture (3:2 ratio) of diastereoisomers (118 mg) as a foam. MS: 603 (MH+).

Workup

  1. customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (94:6:0.3)

Sources & evidence

ORD record
ord-6a9f9afa2f5b4e9fa717d3520ce04b43
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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