Benzylamine → 5-[(2S)-3-(Benzylamino)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenyl-propa-noyl}amino)-3-oxopropyl]-2-(carboxymethoxy)benzoic Acid

HRID 2188428Notes

Reaction equation

HRID 2188428 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].[CH2:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:41]([NH:48][C:14](=[O:15])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 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 701646385-[(2S)-3-(Benzylamino)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenyl-propa-noyl}amino)-3-oxopropyl]-2-(carboxymethoxy)benzoic Acid

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 and benzylamine (31 μL) according to Method A to give a material which was re-purified by reversed phase C-18 HPLC in absence of trifluoroacetic acid to give the title compound (29 mg). 1H-NMR (400 MHz, CD3OD) d 7.78 (s, 1H), 7.36 (dd, J=2.0 Hz, J=8.6 Hz, 1H), 7.30-7.13 (m, 10H), 6.96 (d, J=8.5 Hz, 1H), 4.79 (s, 2H), 4.58 (t, J=6.9 Hz, 1H), 3.11-2.94 (m, 4H), 2.76 (dd, J=10 Hz, J=13.4 Hz, 1H), 1.33 (s, 9H); IR (KBr) 3304, 2979, 1694, 1640 cm−1; HRMS m/z 619.2511 (calc. of monoisotopic mass for C33H37N3O9 gives 619.2530).

Workup

  1. customSynthesis
  2. customto give a material which
  3. customwas re-purified by reversed phase C-18 HPLC in absence of trifluoroacetic acid

Sources & evidence

ORD record
ord-a5cab3f67392440281ae332dde03b63f
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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