Dopamine Hydrochloride → HCID 22976108, compound

HRID 1860324Notes

Reaction equation

HRID 1860324 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[C@@H:10]([CH3:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])(C)(C)C.Cl.[NH2:24][CH2:25][CH2:26][C:27]1[CH:34]=[CH:33][C:31]([OH:32])=[C:29]([OH:30])[CH:28]=1>>[OH:30][C:29]1[CH:28]=[C:27]([CH:34]=[CH:33][C:31]=1[OH:32])[C:6]([NH:8][C@H:9]([C:20]([NH:24][CH2:25][CH2:26][C:27]1[CH:34]=[CH:33][C:31]([OH:32])=[C:29]([OH:30])[CH:28]=1)=[O:22])[C@@H:10]([CH3:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:7]

Participants

3

Reactant 2

HCID 65340Dopamine HydrochlorideHCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 22976108HCID 22976108, compoundYield 120.1%

Procedure

The title compound was prepared from Nα-(tert-butoxycarbonyl)-O-benzyl-L-threonine (2.0 g, 6.5 mmol) following the indications of general procedure F using dopamine hydrochloride (2.4 g, 9.7 mmol). The crude material was purified by flash chromatography eluting with 30% EtOAc/CHCl3 to give 2.8 g (98%) of the desired product as white crystals.

Workup

  1. customThe crude material was purified by flash chromatography
  2. washeluting with 30% EtOAc/CHCl3

Sources & evidence

ORD record
ord-656e226b4bcd492d93fcc5b8a9674158
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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