Diisopropylethylamine → HCID 89573170, compound

HRID 2282859Notes

Reaction equation

HRID 2282859 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]([CH3:55])([C:21]([NH:23][C@H:24]([C:28]([N:30]([C@@H:32]([C@@H:51]([CH3:54])[CH2:52][CH3:53])[C@H:33]([O:49][CH3:50])[CH2:34][C:35](=[O:48])OC3C(F)=C(F)C(F)=C(F)C=3F)[CH3:31])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])[CH3:20])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[CH3:57][O:58][C@@H:59]([C@@H:65]1[CH2:69][CH2:68][CH2:67][NH:66]1)[C@@H:60]([CH3:64])[C:61]([OH:63])=[O:62].C(N(C(C)C)CC)(C)C>ClCCl>[CH:5]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]([CH3:55])([C:21]([NH:23][C@H:24]([C:28]([N:30]([C@@H:32]([C@@H:51]([CH3:54])[CH2:52][CH3:53])[C@H:33]([O:49][CH3:50])[CH2:34][C:35]([N:66]3[CH2:67][CH2:68][CH2:69][C@H:65]3[C@H:59]([O:58][CH3:57])[C@H:60]([C:61]([OH:63])=[O:62])[CH3:64])=[O:48])[CH3:31])=[O:29])[CH:25]([CH3:26])[CH3:27])=[O:22])[CH3:20])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:1]=2[CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 69019103HCID 69019103, compoundHCID 86685740N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methylalanyl-N-[(3R,4S,5S)-3-methoxy-5-methyl-1-oxo-1-(pentafluorophenoxy)heptan-4-yl]-N-methyl-L-valinamide

Product 1

HCID 89573170HCID 89573170, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of #104 (2.00 g, <2.58 mmol, 1 eq.) in dichloromethane (6 mL, 0.4 M) was added a solution of #103 (483 mg, 2.16 mmol, 1 eq.) in dichloromethane (2 mL) followed by diisopropylethylamine (1.35 mL, 7.73 mmol, 3 eq.). The reaction mixture was stirred for 16 hours, then adsorbed onto silica and purified by silica gel chromatography (Gradient: 0% to 20% methanol in dichloromethane) to give #105 (1.67 g, 83%) as a white foam. Fractions containing the desired product with impurities (0.571 g) were collected separately.

Workup

  1. custompurified by silica gel chromatography (Gradient: 0% to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-299cfe968d5b4ad8b668ea1a0e1cd5b9
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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