Dichloromethane → HCID 131731849, compound

HRID 2282826Notes

Reaction equation

HRID 2282826 reaction equation
C1C2C(COC([NH:18][C:19]([CH3:68])([C:21]([NH:23][C@H:24]([C:28]([N:30]([C@@H:32]([C@@H:64]([CH3:67])[CH2:65][CH3:66])[C@H:33]([O:62][CH3:63])[CH2:34][C:35]([N:37]3[CH2:41][CH2:40][CH2:39][C@H:38]3[C@H:42]([O:60][CH3:61])[C@@H:43]([CH3:59])[C:44]([NH:46][C@@H:47]([CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:48]([O:50][CH3:51])=[O:49])=[S:45])=[O:36])[CH3:31])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])[CH3:20])=O)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C.[Cl:74]CCl>>[ClH:74].[CH3:20][C:19]([C:21]([NH:23][C@H:24]([C:28]([N:30]([C@@H:32]([C@@H:64]([CH3:67])[CH2:65][CH3:66])[C@H:33]([O:62][CH3:63])[CH2:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[C@H:42]([O:60][CH3:61])[C@@H:43]([CH3:59])[C:44]([NH:46][C@@H:47]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:48]([O:50][CH3:51])=[O:49])=[S:45])=[O:36])[CH3:31])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])([CH3:68])[NH2:18]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 89573045N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methylalanyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}-2-methyl-3-thioxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Product 1

HCID 131731849HCID 131731849, compoundYield 70%

Procedure

According to general procedure A, from #43 (176 mg, 0.184 mmol, 1 eq.), dichloromethane (4 mL, 0.05 M) and diethylamine (4 mL) was synthesized the crude desired material, which was purified by reverse phase chromatography (Method C). The resulting trifluoroacetic acid salt was dissolved in methanol, treated with a 4 M solution of hydrochloric acid in dioxane, and concentrated in vacuo to give #45 (100 mg, 70%) as a white solid. LC-MS: m/z 734.6 [M+H+], retention time=0.72 minutes; 1H NMR (400 MHz, CD3OD), presumed to be a mixture of rotamers, characteristic signals: δ 7.18-7.31 (m, 5H), 5.41-5.47 and 5.55-5.62 (2 m, total 1H), 3.73 and 3.76 (2 s, total 3H), 3.35 and 3.36 (2 s, total 3H), 3.10 and 3.15 (2 br s, total 3H), 1.62 and 1.64 (2 s, total 3H), 1.53 and 1.55 (2 s, total 3H), [1.25 (d, J=6.6 Hz) and 1.29 (d, J=6.5 Hz), total 3H], 0.84-0.91 (m, 3H).

Workup

  1. customwas purified by reverse phase chromatography (Method C)
  2. dissolutionThe resulting trifluoroacetic acid salt was dissolved in methanol
  3. additiontreated with a 4 M solution of hydrochloric acid in dioxane
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aef34fb9871a4833a239295eafae2487
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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