Acetic Acid → HCID 59975321, compound

HRID 2268386Notes

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.[S:37]1(=[O:45])(=[O:44])[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1.[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:40]1[CH2:41][CH2:42][S:37](=[O:45])(=[O:44])[CH2:38][CH2:39]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 2622301,1-Dioxo-tetrahydro-thiopyran-4-one

HCID 5360545Sodium

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 59975321HCID 59975321, compoundYield 42.8%

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 (305 mg, 0.60 mmol) (example 1), tetrahydro-1λ6-thiopyran-1,1,4-trione (88 mg, 0.60 mmol), sodium triacetoxyborohydrde (200 mg, 0.90 mmol) and acetic acid (43 mg, 0.72 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (96:4:0.2) to give the title compound (160 mg) as a foam. MS: 623 (MH+).

Workup

customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (96:4:0.2)

Sources & evidence

ORD record: ord-a97d62f8823041af9972395fb2b9ae79
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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