(R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid → N-(methoxycarbonyl)-3-methyl-L-valyl-N-[4-({phenyl[4-({1-[(2R)-2-phenyl-2-pyrrolidin-1-ylacetyl]-L-prolyl}amino)benzyl]amino}methyl)phenyl]-L-prolinamide

HRID 923397Notes

Reaction equation

[CH3:1][C:2]([CH3:49])([CH3:48])[C@H:3]([NH:43][C:44](=[O:47])[O:45][CH3:46])[C:4](=[O:42])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10](=[O:41])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C@@H:30]3[CH2:34][CH2:33][CH2:32][NH:31]3)=[O:29])=[CH:23][CH:22]=2)=[CH:14][CH:13]=1.[C:50]1([C@@H:56]([N:60]2[CH2:64][CH2:63][CH2:62][CH2:61]2)[C:57](O)=[O:58])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH3:46][O:45][C:44]([NH:43][C@H:3]([C:4]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:29])[C@@H:30]3[CH2:34][CH2:33][CH2:32][N:31]3[C:57](=[O:58])[C@@H:56]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:60]3[CH2:61][CH2:62][CH2:63][CH2:64]3)=[CH:23][CH:22]=2)=[CH:16][CH:17]=1)=[O:41])=[O:42])[C:2]([CH3:49])([CH3:48])[CH3:1])=[O:47]

Participants

Reactant 2

HCID 1091376(R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid

HCID 59540386Methyl (S)-3,3-dimethyl-1-oxo-1-((S)-2-(4-((phenyl(4-((S)-pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenylcarbamoyl)pyrrolidin-1-yl)butan-2-ylcarbamate

Product 1

HCID 59540240N-(methoxycarbonyl)-3-methyl-L-valyl-N-[4-({phenyl[4-({1-[(2R)-2-phenyl-2-pyrrolidin-1-ylacetyl]-L-prolyl}amino)benzyl]amino}methyl)phenyl]-L-prolinamideYield 60.4%

Procedure

The product from Example 10A (40 mg, 0.060 mmol) and the product of Example 55A (18.4 mg, 0.090 mmol) were processed using the method described in Example 43 to afford 31 mg (60%) of the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.94 (bs, 1H), 9.90 (bs, 1H), 7.46 (m, 3H), 7.41 (m, 2H), 7.27 (m, 3H), 7.15 (m, 4H), 7.02 (m, 3H), 6.61 (d, J=8.2 Hz, 2H), 6.52 (t, J=7.3 Hz, 1H), 4.55 (bs, 4H), 4.38 (m, 1H), 4.27 (m, 1H), 4.17 (m, 2H), 3.79 (m, 1H), 3.72 (m, 1H), 3.58 (m, 1H), 3.49 (s, 3H), 3.40 (m, 1H), 2.43 (m, 3H), 2.29 (m, 2H), 2.09 (m, 1H), 1.95 (m, 3H), 1.89 (m, 4H), 1.57 (m, 3H), 0.91 (s, 9H).

Sources & evidence

ORD record: ord-651cb57344b748bb997239ae2be4bb31
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278922B2

Reaction notes

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