Hydrochloric Acid → HCID 136341202, compound

HRID 346115Notes

Reaction equation

HRID 346115 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:34])[C:5]2[N:6]=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][N:15](C(OCC3C=CC=CC=3)=O)[C@H:16]([C:21]([O-:23])=[O:22])[C@H:17]([CH2:19][CH3:20])[CH3:18])[C:9]=2[N:10]=1.[ClH:35]>CO.O1CCCC1.[Pd]>[ClH:35].[NH2:1][C:2]1[NH:3][C:4](=[O:34])[C:5]2[N:6]=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][NH:15][C@H:16]([C:21]([OH:23])=[O:22])[C@H:17]([CH2:19][CH3:20])[CH3:18])[C:9]=2[N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136341203HCID 136341203, compound

Product 1

HCID 136341202HCID 136341202, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-methoxy]-ethyl-N-[(benzyloxy)carbonyl]-L-isoleucinate (1.11 g, 2.2 mmol) in methanol-tetrahydro furan (1:1, 50 ml) was treated with 0.5N hydrochloric acid (5 ml) and 5% palladium on charcoal (0.30 g; MCB Reagents). The mixture was hydrogenated on a Parr hydrogenator at 50 psi for 11 hours, filtered through a Celite pad and the filtrate was concentrated in vacuo to give 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl-L-isoleucinate hydrochloride (0.86 g, 92%) as an off-white solid; mp 180°-182° C. (effervescent softening ca. 150° C.):

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0d8b3141a8444e22812eb33d86c01285
Source dataset
uspto-grants-1991_10
Patent number
US05061708

Reaction notes

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