HCID 14556109, compound → HCID 9842268, compound

HRID 1607347Notes

Reaction equation

HRID 1607347 reaction equation
OC1C=CC(CC2C3CCCCC=3CCN2)=CC=1.[NH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[S:30][CH:31]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH:32]([OH:36])[C:33]([OH:35])=[O:34]>Cl>[NH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[S:30][CH:31]([C:37]1[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=1)[CH:32]([OH:36])[C:33]([OH:35])=[O:34]

Participants

3

Reactant 1

HCID 14556109HCID 14556109, compound

Product 1

HCID 9842268HCID 9842268, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(-)-β-[(2-Amino-1-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid (-)-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, 4.9 g (0.0077 mol) was decomposed in 60 mL of 1N HCl. The resulting suspension was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate solutions were dried (MgSO4) and removal of the solvent gave 2.9 g of crude (-)-β-[(2-amino-1-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid. Recrystallization from CHCl3 (10 mL) overnight afforded 2.37 g (82.8%) of (-)-β-[(2-amino-1-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, mp 142°-144°. The analytical sample was recrystallized from benzene, mp 143°-145°, [α]D25 -268.32° (C 0.476, MeOH.

Workup

  1. extractionThe resulting suspension was extracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined ethyl acetate solutions were dried
  3. custom(MgSO4) and removal of the solvent

Sources & evidence

ORD record
ord-59a565392abc4a6291ae1485f724fe5d
Source dataset
uspto-grants-1989_09
Patent number
US04864058

Reaction notes

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