Hydrochloric Acid → Acetic acid (2R,3R,4R,5S)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethyl amino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester hydrochloride

HRID 655120Notes

Reaction equation

HRID 655120 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([C:10]2[O:14][N:13]=[C:12]([CH2:15][CH3:16])[CH:11]=2)[O:8][C@@H:7]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:27])=[N:21][C:22]=3[Cl:26])[C@@H:6]1[O:28][C:29](=[O:31])[CH3:30])(=[O:3])[CH3:2].[NH2:32][C@@H:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:34][OH:35].CCN(C(C)C)C(C)C.Cl>ClCCCl>[ClH:26].[C:1]([O:4][C@@H:5]1[C@@H:9]([C:10]2[O:14][N:13]=[C:12]([CH2:15][CH3:16])[CH:11]=2)[O:8][C@@H:7]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:27])=[N:21][C:22]=3[NH:32][C@@H:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:34][OH:35])[C@@H:6]1[O:28][C:29](=[O:31])[CH3:30])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 447213phenylalaninol, (S)-HCID 10950783acetic acid (2R,3R,4R,5S)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester

Product 1

HCID 86623488Acetic acid (2R,3R,4R,5S)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethyl amino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture comprising acetic acid (2R,3R,4R,5S)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester (WO 99/38877) (1 g, 2.13 mmol), (S)-2-amino-3-phenyl-propan-1-ol (0.321 g, 2.13 mmol) and DIPEA (0.275 g, 2.13 mmol) in DCE (5 mL) is stirred under an inert atmosphere of argon overnight. After cooling to room temperature (RT), 1 M HCl is added, the organic portion is separated and concentrated in vacuo to afford the title compound which is used in the next step without further purification. (MH+585.1)

Workup

  1. additionis added
  2. customthe organic portion is separated
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce25e97303a7476c9d5549dbc70ce080
Source dataset
uspto-grants-2011_12
Patent number
US08071565B2

Reaction notes

Loading…