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(R)-2-morpholino-2-phenylacetic acid → N-(methoxycarbonyl)-3-methyl-L-valyl-N-[4-({[4-({1-[(2R)-2-morpholin-4-yl-2-phenylacetyl]-L-prolyl}amino)benzyl](phenyl)amino}methyl)phenyl]-L-prolinamide

HRID 923399
Notes
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Reaction equation

HRID 923399 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.[O:50]1[CH2:55][CH2:54][N:53]([C@H:56]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:57](O)=[O:58])[CH2:52][CH2:51]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]([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]([N:53]3[CH2:54][CH2:55][O:50][CH2:51][CH2:52]3)[C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)=[CH:23][CH:22]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:16][CH:17]=1)=[O:41])=[O:42])[C:2]([CH3:49])([CH3:48])[CH3:1])=[O:47]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 1090521(R)-2-morpholino-2-phenylacetic acidHCID 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 59540322N-(methoxycarbonyl)-3-methyl-L-valyl-N-[4-({[4-({1-[(2R)-2-morpholin-4-yl-2-phenylacetyl]-L-prolyl}amino)benzyl](phenyl)amino}methyl)phenyl]-L-prolinamideYield 67%

Procedure

The product from Example 10A (40 mg, 0.060 mmol) and the product of Example 57A (19.9 mg, 0.090 mmol) were processed using the method described in Example 43 to afford 35 mg (67%) of the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.80 (s, 1H), 9.78 (s, 1H), 7.35 (m, 3H), 7.28 (m, 2H), 7.14 (m, 3H), 6.97 (m, 4H), 6.88 (m, 3H), 6.46 (d, J=8.1 Hz, 2H), 6.37 (t, J=7.2 Hz, 1H), 4.40 (bs, 4H), 4.22 (m, 1H), 4.11 (m, 1H), 4.05 (m, 2H), 3.67 (m, 1H), 3.57 (m, 1H), 3.43 (m, 1H), 3.34 (s, 3H), 3.30 (m, 3H), 3.24 (m, 2H), 2.49 (s, 8H), 2.22 (m, 2H), 2.12 (m, 2H), 1.92 (m, 1H), 1.79 (m, 3H), 1.62 (m, 4H), 0.77 (s, 9H).

Sources & evidence

ORD record
ord-4f161e81541c47d4a419371aadfdf876
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278922B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes