HCID 21566371, compound → HCID 70161035, compound

HRID 2188441Notes

Reaction equation

HRID 2188441 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([C:47]2[CH:56]=[CH:55][CH:54]=[C:49]([C:50]([NH:52][NH2:53])=[O:51])[C:48]=2[OH:57])[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]([NH:53][NH:52][C:50]([C:49]1[C:48]([OH:57])=[C:47]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:56]=[CH:55][CH:54]=1)=[O:51])=[O:15])[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 21566371HCID 21566371, 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 70161035HCID 70161035, compoundYield 23.8%

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 (93 mg, 0.17 mmol) and 3-phenylsalicylic acid hydrazide (45 mg, 0.20 mmol) according to Method C with HPLC purification to give the title compound (30 mg). 1H-NMR (400 MHz, CD3OD) d 4.80 (s, 2H), 4.27 (dd, J=4.9 Hz, J=9.8 Hz, 1H), 3.04 (m, 1H), 2.94 (m, 1H), 2.72 (dd, J=9.3 Hz, J=13.7 Hz, 1H), 1.34 (s, 9H); IR (KBr) 3280, 1694, 1653 cm−1; HRMS m/z 740.2666 (calc. of monoisotopic mass for C39H40N4O11 gives 740.2694).

Workup

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

Sources & evidence

ORD record
ord-20c2f953d18042e8a64026041e561874
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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