Hydrochloric Acid → HCID 23322550, compound

HRID 279796Notes

Reaction equation

HRID 279796 reaction equation
[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])[C:3]1=[O:18].[ClH:19]>C(OCC)(=O)C>[ClH:19].[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:10][C:11]([OH:13])=[O:12])[C:3]1=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13608303HCID 13608303, compound

Product 1

HCID 23322550HCID 23322550, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-1-t-butoxycarbonylmethylperhydroazocin-2-one is treated with 4N HCl in ethyl acetate to afford 3-amino-1-carboxymethylperhydroazocin-2-one hydrochloride. An aqueous solution of this hydrochloride and 3-5 equivalents of an α-ketoacid from Table III is adjusted to pH 6.5 with sodium hydroxide and treated with 3 equivalents of sodium cyanoborohydride for 18 hours. The product is absorbed on a strong acid ion exchange resin and eluted with 5% pyridine in water. Lyophilization affords the products of Formula I listed in Table II in which R2, R3 =H and R, R4 =OH.

Sources & evidence

ORD record
ord-b86a0943dc574db3ba4ece856fc6980d
Source dataset
uspto-grants-1986_05
Patent number
US04587050

Reaction notes

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