1,2-Dichloroethane → HCID 69314488, compound

HRID 1391720Notes

Reaction equation

HRID 1391720 reaction equation
[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C@@H:7]([NH:16][CH2:17][C@@H:18]([OH:30])[C@@H:19]([NH2:29])[CH2:20][C:21]2[CH:26]=[C:25](F)[CH:24]=[C:23](F)[CH:22]=2)[CH2:6]1)[CH:2]=[CH2:3].[C:31]([NH:34][C@:35]1([CH:48]([CH2:50][CH3:51])[CH3:49])[CH2:39][CH2:38][N:37]([C@@H:40]([CH2:44][CH:45]=[CH2:46])[C:41](O)=[O:42])[C:36]1=[O:47])(=[O:33])[CH3:32].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:31]([NH:34][C@:35]1([CH:48]([CH2:50][CH3:51])[CH3:49])[CH2:39][CH2:38][N:37]([C@@H:40]([CH2:44][CH:45]=[CH2:46])[C:41]([NH:29][C@H:19]([C@H:18]([OH:30])[CH2:17][NH:16][C@@H:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=3)[C@H:5]([O:4][CH2:1][CH:2]=[CH2:3])[CH2:6]2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:42])[C:36]1=[O:47])(=[O:33])[CH3:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59676141HCID 59676141, compoundHCID 69315002HCID 69315002, compound

Product 1

HCID 69314488HCID 69314488, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step N (1): (2R,3S)-1-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol (20 mg, 0.05 mmol) from step E (2), (S)-2-((S)-3-acetamido-3-sec-butyl-2-oxopyrrolidin-1-yl)pent-4-enoic acid (14 mg, 0.048 mmol) from step L (7), EDC (10 mg, 0.05 mmol), HOBt (7 mg, 0.05 mmol), DIEA (40 μL, 0.24 mmol) were mixed in 2 mL of DMF. The mixture was stirred at RT for 24 h. Purified with reverse phase Prep-HPLC to give 14.1 mg of (S)-2-((S)-3-acetamido-3-sec-butyl-2-oxopyrrolidin-1-yl)-N-((2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-yl)pent-4-enamide as a light brown viscous residue (TFA salt): LC-MS (M+H)+=661.37, 1H NMR (300 MHz, CDCl3) δ ppm 0.82 (t, J=5.86 Hz, 2H) 0.89-1.69 (m, 5H) 1.86-2.04 (m, 4H) 2.35-2.90 (m, 5H) 3.05-4.17 (m, 19H) 4.57 (d, J=6.59 Hz, 1H) 4.75 (d, J=4.76 Hz, 1H) 4.87-4.98 (m, 1H) 5.12-5.34 (m, 1H) 5.38-5.57 (m, 1H) 5.78-5.94 (m, 1H) 6.01 (s, 1H) 6.84-6.95 (m, 1H) 7.02-7.36 (m, 8H) 7.70 (d, J=9.15 Hz, 1H).

Workup

  1. customPurified with reverse phase Prep-HPLC

Sources & evidence

ORD record
ord-9ce733eb3953484eaef9a0bcc8ce2aa1
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

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