623-33-6 → HCID 178461609, compound

HRID 2297372Notes

Reaction equation

HRID 2297372 reaction equation
CC[O:3]C(C[NH3+])=O.[Cl-].C([O-])(=O)C.[Na+].[OH:14][C:15]1[N:20]=[CH:19][NH:18][C:17]2=[C:21]([C@@H:24]3[NH:31][C@H:28]([CH2:29]O)[C@@H:26]([OH:27])[CH2:25]3)[CH:22]=[N:23][C:16]=12>CO>[OH:14][C:15]1[N:20]=[CH:19][NH:18][C:17]2=[C:21]([C@@H:24]3[NH:31][C@H:28]([CH3:29])[C@@H:26]([OH:27])[C@H:25]3[OH:3])[CH:22]=[N:23][C:16]=12

Participants

5

Reactant 3

HCID 12175623-33-6HCID 517045Sodium AcetateHCID 178521050HCID 178521050, compound

Product 1

HCID 178461609HCID 178461609, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Glycine hydrochloride ethyl ester (0.76 g) and sodium acetate (0.9 g) were added to a stirred solution of the product from Example 1.3 (0.51 g) in methanol (10 ml). The mixture was stirred at room temperature for 16 h and then concentrated to dryness. Chromatography of the residue gave the (1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-[1-cyano-2-(ethoxycarbonylmethylamino) ethenyl]-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (4) (0.48) g as a diastereomeric mixture.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-31fcd66e4107487e85f2a447c647dbe9
Source dataset
uspto-grants-2002_12
Patent number
US06492347B2

Reaction notes

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