Hydrochloric Acid → (3S,6S,10aS)-6-amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid

HRID 1824420Notes

Reaction equation

HRID 1824420 reaction equation
C[O:2][C:3]([CH:5]1[N:9]2[C:10](=[O:17])[CH:11]([NH2:16])[CH2:12][CH:13]=[CH:14][CH2:15][CH:8]2[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[NH2:16][C@@H:11]1[C:10](=[O:17])[N:9]2[C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][C@H:8]2[CH2:15][CH:14]=[CH:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 695845816-Amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester

Product 1

HCID 69584518(3S,6S,10aS)-6-amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 6-amino-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester, 8, (1.4 g, 5.2 mmol) in THF/water (3:1) is added LiOH (1.1 eq) and the solution is stirred overnight. The reaction is treated with 1 N HCl to pH 4. The mixture is then frozen and lyophilized to a pale yellow powder, which can be used directly in the next step.

Workup

  1. temperatureThe mixture is then frozen

Sources & evidence

ORD record
ord-d165c1a2325b46768aeebb89839745fb
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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