HCID 14556109, compound → HCID 9842268, compound

HRID 1607346Notes

Reaction equation

HRID 1607346 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, compoundYield 96.2%

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, 5.0 g (0.0079 mol) was decomposed in 60 mL 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 3.25 g of crude acid of the title. Recrystallization from CHCl3 (10 mL) overnight afforded 2.81 g (96.2%) of (+)-β-[(2-amino-1-naphthaleneyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, mp 143°-145°. The analytical sample was recrystallized from benzene, mp 143°-145°, [α]D25 +269.51° (C 0.52, 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
  4. customgave 3.25 g of crude acid of the title
  5. customRecrystallization from CHCl3 (10 mL) overnight

Sources & evidence

ORD record
ord-3a3d865f171542ceafc70a853d3b4ec7
Source dataset
uspto-grants-1989_09
Patent number
US04864058

Reaction notes

Loading…