HCID 1712812, compound → HCID 57291343, compound

HRID 2188446Notes

Reaction equation

HRID 2188446 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](O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:41]1([CH2:47][CH2:48][CH2:49][O:50][NH2:51])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[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](=[O:15])[NH:51][O:50][CH2:49][CH2:48][CH2:47][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[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 1712812HCID 1712812, compoundHCID 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 57291343HCID 57291343, compoundYield 44.4%

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-phenylpropoxyamine (41 mg, 0.22 mmol) according to Method C with HPLC purification to give the title compound (53 mg). 1H-NMR (400 MHz, CD3OD) d 7.57 (s, 1H), 6.94 (d, J=8.3 Hz, 1H), 4.28 (m, 1H), 3.65 (m, 2H), 3.04 (dd, J=4.9 Hz, J=13.9 Hz, 1H), 2.97 (m, 1H), 2.73 (dd, J=9.6 Hz, J=13.8 Hz, 1H), 2.65 (t, J=7.7 Hz, 2H), 1.78 (m, 2H), 1.37 (s, 3H), 1.36 (s, 6H); IR (KBr) 3293, 2949, 1681, 1651 cm−1; HRMS m/z 663.2806 (calc. of monoisotopic mass for C35H41N3O10 gives 663.2792).

Workup

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

Sources & evidence

ORD record
ord-51ba6f74d7ef43f288b45a6cbe3ea69a
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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