Diisopropylethylamine → HCID 68759365, compound

HRID 1628303Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:10]3[CH2:11][CH2:12][NH:13][C:14]=3[CH:15]=2)=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:44]([O:48][C:49]([C@@H:51]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:52](O)=[O:53])=[O:50])([CH3:47])([CH3:46])[CH3:45].CCN(C(C)C)C(C)C>CN(C=O)C>[C:44]([O:48][C:49]([C@@H:51]([CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)[C:52]([N:13]1[C:14]2[CH:15]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH:8]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:10]=2[CH2:11][CH2:12]1)=[O:53])=[O:50])([CH3:47])([CH3:45])[CH3:46]

Participants

Conditions

Temperature: 60 °C

Procedure

To a 500 ml flask was added methyl 6-(pyridin-4-yl)indoline-4-carboxylate 54.1.C (1.98 g, 7.81 mmole), of HBTU (5.92 g, 15.6 mmole), (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid 3.11 g, 11.7 mmole, available from Aldrich) 50 ml of DMF and DIEA (4.08 ml, 23.4 mmole). The reaction was stirred at 60° C. for 6 hours, at which time the crude reaction was partitioned between 1000 ml of EtAc and 500 ml of water. The solvent was removed and the crude purified using a silica gel column (Elutent; 50/50 EtAc/Hex) to give (S)-methyl 1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylate 54.1.D as a yellow solid (2.05 g, 52.3% yield).

Workup

customreaction
customwas partitioned between 1000 ml of EtAc and 500 ml of water
customThe solvent was removed
customthe crude purified

Sources & evidence

ORD record: ord-30acbc13b219455f9338e67dae600f6d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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