Diethylamine → N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[2-(cyclohepta-2,4,6-trien-1-yl)ethyl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

HRID 74803Notes

Reaction equation

HRID 74803 reaction equation
[CH:1]1([CH2:8][CH2:9][NH:10][C:11](=[O:59])[C@H:12]([CH3:58])[C@H:13]([C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:57])[CH2:22][C@@H:23]([O:55][CH3:56])[C@@H:24]([N:29]([CH3:54])[C:30](=[O:53])[C@H:31]([CH:50]([CH3:52])[CH3:51])[NH:32]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[C@@H:25]([CH3:28])[CH2:26][CH3:27])[O:14][CH3:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[CH:2]1.C(NCC)C>ClCCl>[CH:1]1([CH2:8][CH2:9][NH:10][C:11](=[O:59])[C@H:12]([CH3:58])[C@H:13]([C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:57])[CH2:22][C@@H:23]([O:55][CH3:56])[C@@H:24]([N:29]([CH3:54])[C:30](=[O:53])[C@H:31]([CH:50]([CH3:51])[CH3:52])[NH2:32])[C@@H:25]([CH3:28])[CH2:26][CH3:27])[O:14][CH3:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 89582252N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[2-(cyclohepta-2,4,6-trien-1-yl)ethyl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N~2~-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valinamide

Product 1

HCID 86685760N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[2-(cyclohepta-2,4,6-trien-1-yl)ethyl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure A, from #175 (560 mg, 0.690 mmol, 1 eq.) in dichloromethane (9 mL), and N,N-diethylamine (6.0 mL), was synthesized the crude desired compound, which was purified by by silica gel chromatography (Gradient: 0 to 50% methanol in dichloromethane) to afford #176 (351 mg, 87%) as a yellow oil. LC-MS (Protocol Q1): m/z 589.5 [M+H+], retention time=0.72 minutes.

Workup

  1. customwas synthesized the crude desired compound, which
  2. customwas purified by by silica gel chromatography (Gradient: 0 to 50% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ed8993fb51a344bba9ce9e84608caca8
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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