Acetic Acid → HCID 59975309, compound

HRID 2268387Notes

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

Participants

Reactant 4

HCID 176Acetic Acid

HCID 90583N-Benzoyl-4-piperidone

HCID 5049666Sodium triacetoxyborohydride

HCID 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 59975309HCID 59975309, compoundYield 70.3%

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 (310 mg, 0.63 mmol) (example 1), 1-benzoyl-4-piperidinone (128 mg, 0.63 mmol), sodium triacetoxyborohydride (200 mg, 0.90 mmol) and acetic acid (45 mg, 0.74 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (92:8:0.4) to give the title compound (300 mg) as an oil. MS: 679 (MH+).

Workup

customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (92:8:0.4)

Sources & evidence

ORD record: ord-105a5a7b70394ee393e10980c7db2938
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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