Diisopropylethylamine → HCID 131737020, compound
Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:34][C@@H:35]([CH2:60][OH:61])[C:36]([NH:38][C@@H:39]([C@H:50]([OH:59])[C:51]1[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=1)[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])=[O:37].[O:62]1[CH2:67][CH2:66][N:65]([CH2:68][C:69](O)=[O:70])[CH2:64][CH2:63]1>CN(C=O)C>[OH:59][C@H:50]([C:51]1[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=1)[C@H:39]([NH:38][C:36](=[O:37])[C@@H:35]([NH:34][C:69](=[O:70])[CH2:68][N:65]1[CH2:66][CH2:67][O:62][CH2:63][CH2:64]1)[CH2:60][OH:61])[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41]Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 4389684-Morpholineacetic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 130394423(2S,3R)-benzyl 2-((S)-2-amino-3-hydroxypropanamido)-3-hydroxy-3-(4-methoxyphenyl)propanoateProduct 1
Reagents, catalysts & solvents 1
Procedure
Sequentially HATU (509 mg, 1.34 mmol) and DIEA (0.78 mL, 4.5 mmol) were added to a 0° C. solution of (2S,3R)-benzyl 2-((S)-2-amino-3-hydroxypropanamido)-3-hydroxy-3-(4-methoxyphenyl)propanoate (HCl salt, 474 mg, 1.12 mmol) and 2-morpholinoacetic acid (162 mg, 1.12 mmol) in DMF (8 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 30 min. The mixture was concentrated and the residue was washed with EtOAc to afford (2S,3R)-benzyl 3-hydroxy-2-((S)-3-hydroxy-2-(2-morpholinoacetamido)propanamido)-3-(4-methoxyphenyl)propanoate (349 mg, 67% yield) as a colorless solid.
Workup
- concentrationThe mixture was concentrated
- washthe residue was washed with EtOAc
Sources & evidence
- ORD record
- ord-882c9b9458b04094a8261411075c3b99
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434761B2
Reaction notes
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