Dopamine Hydrochloride → HCID 22976102, compound

HRID 1860329Notes

Reaction equation

HRID 1860329 reaction equation
C1C2C(COC(N[C@H](C(O)=O)CSC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=O)C3C(=CC=CC=3)C=2C=CC=1.Cl.NCC[C:48]1[CH:55]=[CH:54][C:52](O)=[C:50]([OH:51])[CH:49]=1.C1C2C(CO[C:71]([NH:73][C@H:74]([C:96]([NH:98][CH2:99][CH2:100][C:101]3[CH:108]=[CH:107][C:105]([OH:106])=[C:103]([OH:104])[CH:102]=3)=[O:97])[CH2:75][S:76][C:77]([C:90]3[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=3)([C:84]3[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=3)[C:78]3[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=3)=[O:72])C3C(=CC=CC=3)C=2C=CC=1.[F:109]C1(O)C=CC=CC1C(O)=O>>[F:109][C:48]1[CH:55]=[CH:54][CH:52]=[C:50]([OH:51])[C:49]=1[C:71]([NH:73][C@H:74]([C:96]([NH:98][CH2:99][CH2:100][C:101]1[CH:108]=[CH:107][C:105]([OH:106])=[C:103]([OH:104])[CH:102]=1)=[O:97])[CH2:75][S:76][C:77]([C:84]1[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=1)([C:90]1[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=1)[C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1)=[O:72]

Participants

5

Reactant 4

HCID 65340Dopamine HydrochlorideHCID 128239N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 22976136HCID 22976136, compoundHCID 69566153HCID 69566153, compound

Product 1

HCID 22976102HCID 22976102, compound

Procedure

Commercially available Nα-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (1.7 g, 2.9 mmol) was coupled with dopamine hydrochloride (825 mg, 4.3 mmol) according to the indications of general procedure F. The crude N-[Nα-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteinyl]dopamine (618 mg, 0.86 mmol) was deprotected according to the indications of general procedure G. The resulting intermediate was then coupled with 2-fluorosalicylic acid (202 mg, 1.3 mmol) according to the indications of general procedure D. The final product was purified by flash chromatography using 99% CH2Cl2/1% AcOH and successively 5% then 10% AcOEt/CH2C2/1% AcOH to yield the desired derivative (260 mg, 48%) as white crystals.

Workup

  1. customThe final product was purified by flash chromatography
  2. custom10% AcOEt/CH2C2/1% AcOH to yield the desired derivative (260 mg, 48%) as white crystals

Sources & evidence

ORD record
ord-595353852ea04cf69381da409468d959
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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