L-Phenylalanine → Dopamine

HRID 1678100Notes

Reaction equation

HRID 1678100 reaction equation
N[C@H](C(O)=[O:11])CC1C=CC=CC=1.C1(N[C@H](C(O)=O)C)CCCCC1.C1C2C(=CC=CC=2)C=CC=1N[C@H](C(O)=O)C.N[C@H](C(O)=O)CCC1C=CC=CC=1.N[CH:55]([CH2:59][CH2:60][CH2:61][CH2:62]CC)[C:56]([OH:58])=O.[CH3:65][C:66]#[N:67]>>[NH2:67][CH2:66][CH2:65][C:60]1[CH:61]=[CH:62][C:56]([OH:58])=[C:55]([OH:11])[CH:59]=1

Participants

7

Reactant 6

HCID 6140L-Phenylalanine2×HCID 6342AcetonitrileHCID 695222-Aminooctanoic acid2×HCID 2724505(S)-2-amino-4-phenylbutanoic acid2×HCID 12003067(S)-2-(Cyclohexylamino)propanoic acid2×HCID 18605878N-Naphthalen-2-yl-L-alanine2×

Product 1

HCID 681Dopamine

Procedure

Product characterization: Reverse phase HPLC: linear gradient from 15 to 65% MeCN in 15 minutes using a Symmetry C18 column (150×4.6 mm×5 μm, 100 Å, Waters), compound 6a tr: 7.83 min, compound 6b tr: 9.36 min, compound 6c tr: 9.61 min, compound 6d tr: 11.75 min, compound 6e tr: 7.85 min, compound 6f tr: 10.58 min. (Confirmed by HPLC-MS). Mass spectrometry (HPLC-MS): compound 6a: 516.5 Da, compound 6b: 522.5 Da, compound 6c: 566.2 Da, compound 6d: 640.4 Da, compound 6e: 530.3 Da, compound 6f: 510.4 Da. Yield (after purification): compound 6a: 10.8%, compound 6b: 7.2%, compound 6c: 10.9%, compound 6d: 9.6%, compound 6e: 9.1%, compound 6f: 8.2%.

Workup

  1. custom10.58 min. (Confirmed by HPLC-MS)
  2. customYield
  3. custom(after purification)

Sources & evidence

ORD record
ord-5ae56b2cc7c24bcf9cd73f502be7a16d
Source dataset
uspto-grants-2011_08
Patent number
US08008492B2

Reaction notes

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