Homoveratrylamine → HCID 57066266, compound

HRID 2188448Notes

Reaction equation

HRID 2188448 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[C:20]([C:30]([O:32]C)=[O:31])[CH:19]=1)[C:14]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:41][O:42][C:43]1[CH:44]=[C:45]([CH:49]=[CH:50][C:51]=1[O:52][CH3:53])[CH2:46][CH2:47][NH2:48]>>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][C@H:13]([C:14]([NH:48][CH2:47][CH2:46][C:45]1[CH:49]=[CH:50][C:51]([O:52][CH3:53])=[C:43]([O:42][CH3:41])[CH:44]=1)=[O:16])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH:19]=1)[C:30]([OH:32])=[O:31])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 8421HomoveratrylamineHCID 57019224(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid

Product 1

HCID 57066266HCID 57066266, compoundYield 9.6%

Procedure

Synthesis was performed from (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid (100 mg, 0.18 mmol) and 3,4-dimethoxyphenethylamine (52 mg, 0.29 mmol) according to Method C with HPLC purification to give the title compound (12 mg). 1H-NMR (400 MHz, CD3OD) δ 1.38 (s, 9H) 2.68 (t, 2H) 2.72-3.09 (m, 4H) 3.29-3.44 (m, 2H) 3.80 (s, 3H) 3.85 (s, 3H) 4.25 (m, 1H) 4.52 (m, 1H) 4.79 (s, 2H) 6.74 (d, 1H) 6.84 (s, 1H) 6.87 (d, 1H) 7.06 (d, 1H) 7.17-7.38 (m, 6H) 7.73 (s, 1H); HRMS m/z 693.2904 (calc of monoisotopic mass for C36H43N3O11 gives 693.2898).

Workup

  1. customSynthesis
  2. customaccording to Method C with HPLC purification

Sources & evidence

ORD record
ord-6fa1c44f3a404ddca70d0fefa42da6ce
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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