Diethylamine → HCID 71569003, compound

HRID 2282871Notes

Reaction equation

HRID 2282871 reaction equation
C1C2C(COC([NH:18][CH2:19][C:20]([CH3:69])([CH3:68])[C:21]([NH:23][C@H:24]([C:28]([N:30]([CH3:67])[C@@H:31]([C@@H:63]([CH3:66])[CH2:64][CH3:65])[C@H:32]([O:61][CH3:62])[CH2:33][C:34]([N:36]3[CH2:40][CH2:39][CH2:38][C@H:37]3[C@H:41]([O:59][CH3:60])[C@@H:42]([CH3:58])[C:43]([NH:45][C@H:46]([C:54]([O:56][CH3:57])=[O:55])[CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:44])=[O:35])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])=O)C3C(=CC=CC=3)C=2C=CC=1.C1COCC1.C(NCC)C>>[NH2:18][CH2:19][C:20]([CH3:69])([CH3:68])[C:21]([NH:23][C@H:24]([C:28]([N:30]([CH3:67])[C@@H:31]([C@@H:63]([CH3:66])[CH2:64][CH3:65])[C@H:32]([O:61][CH3:62])[CH2:33][C:34]([N:36]1[CH2:40][CH2:39][CH2:38][C@H:37]1[C@H:41]([O:59][CH3:60])[C@@H:42]([CH3:58])[C:43]([NH:45][C@H:46]([C:54]([O:56][CH3:57])=[O:55])[CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:44])=[O:35])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22]

Participants

4

Reactant 3

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 86685747methyl N-[(2R,3R)-3-{(2S)-1-[(3R,4S,5S)-4-{[N-(3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2,2-dimethylpropanoyl)-L-valyl] (methyl)amino}-3-methoxy-5-methylheptanoyl]pyrrolidin-2-yl}-3-methoxy-2-methylpropanoyl]-L-phenylalaninate

Product 1

HCID 71569003HCID 71569003, compoundYield 56.1%

Procedure

To a stirring solution of #125 (235 mg, 0.246 mmol, 1.00 eq.) in 2 mL of THF, (1 mL, 10 mM, 40.6 eq.) of diethylamine was added. The reaction was allowed to stir at room temperature for 3 hours. Reaction was concentrated in vacuo and the residue was purified by silica chromatography (Gradient: 0%-30% methanol in ethyl acetate) producing #126 (101 mg, 56%) as a white solid. LC-MS (Protocol Q): m/z 732.2 [M+H+] retention time=1.32 minutes. 1H NMR (400 MHz, DMSO-d6), δ 8.51 (dd), 8.28 (d), 7.15-7.29 (m), 5.77 (s), 4.55-4.77 (m), 4.44-4.54 (m), 3.94-4.10 (m), 3.73-3.79 (m), 3.66 (d), 3.49-3.60 (m), 3.40-3.48 (m), 3.10-3.36 (m), 3.00-3.09 (m), 2.83-2.98 (m), 2.57-2.77 (m), 2.19-2.46 (m), 1.87-2.14 (m), 1.61-1.86 (m), 1.36-1.55 (m), 1.23-1.36 (m), 1.12-1.22 (m), 0.97-1.11 (m), 0.82-0.96 (m), 0.73-0.81 (m).

Workup

  1. customReaction
  2. concentrationwas concentrated in vacuo
  3. customthe residue was purified by silica chromatography (Gradient: 0%-30% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-80e15d9715af45ecaa1291bfeaa8830a
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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