HCID 21971826, compound → HCID 53978594, compound

HRID 369372Notes

Reaction equation

HRID 369372 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:35])[CH2:16][NH:17][C@H:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][C:22]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:23][CH:24]=3)[CH2:19]2)=[CH:11][C:10]=1[CH2:36][CH2:37][O:38]CC1C=CC=CC=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[OH:35][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:36][CH2:37][OH:38])[CH:11]=1)[CH2:16][NH:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:23][CH:24]=2)[CH2:19]1

Participants

4

Reactant 1

HCID 21971826HCID 21971826, compound

Product 1

HCID 53978594HCID 53978594, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 2-[(2S)-2-[[(2RS)-2-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxyethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (200 mg) and 10% palladium on activated carbon (30 mg) was suspended in acetic acid (1.5 ml), and the suspension was stirred for 6 hours at room temperature under a hydrogen atmosphere. The reaction mixture was filtrated to remove the catalyst, and the filtrate was concentrated in vacuo. Purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: dichloromethane/ethanol=10/1) gave ethyl 2-[(2S)-2-[[(2RS)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)phenyl]ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (Compound 3) (120 mg) as an amorphous.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: dichloromethane/ethanol=10/1)

Sources & evidence

ORD record
ord-0365da24db5a479b8e67503ca63edc79
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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