N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl-N-{(3R,4S,5S)-3-methoxy-1-[(2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(2-phenylethyl)amino]-3-thioxopropyl}pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide → HCID 86685727, compound

HRID 2282822Notes

Reaction equation

HRID 2282822 reaction equation
C1C2C(CO[C:16]([N:18](C)[C@H:19]([C:23]([NH:25][C@H:26]([C:30]([N:32]([C@@H:34]([C@@H:62]([CH3:65])[CH2:63][CH3:64])[C@H:35]([O:60][CH3:61])[CH2:36][C:37]([N:39]3[CH2:43][CH2:42][CH2:41][C@H:40]3[C@H:44]([O:58][CH3:59])[C@@H:45]([CH3:57])[C:46]([NH:48][CH2:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[S:47])=[O:38])[CH3:33])=[O:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[CH:20]([CH3:22])[CH3:21])=O)C3C(=CC=CC=3)C=2C=CC=1>ClCCl.C(NCC)C>[CH3:16][NH:18][C@H:19]([C:23]([NH:25][C@H:26]([C:30]([N:32]([C@@H:34]([C@@H:62]([CH3:65])[CH2:63][CH3:64])[C@H:35]([O:60][CH3:61])[CH2:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[C@H:44]([O:58][CH3:59])[C@@H:45]([CH3:57])[C:46]([NH:48][CH2:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[S:47])=[O:38])[CH3:33])=[O:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 86685728N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl-N-{(3R,4S,5S)-3-methoxy-1-[(2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(2-phenylethyl)amino]-3-thioxopropyl}pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Product 1

HCID 86685727HCID 86685727, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

According to general procedure A, from #35 (465 mg, 0.502 mmol, 1 eq.) in dichloromethane (5 mL, 0.1 M) and diethylamine (5 mL) was synthesized the crude desired material, which was purified by silica gel chromatography (Gradient: 0% to 10% methanol in dichloromethane) to give #36 (310 mg, 88%) as a solid. LC-MS: m/z 704.6 [M+H+], retention time=0.74 minutes; HRMS: m/z calculated for C38H66N5O5S: 704.4779. found: 704.477 [M+H+]; 1H NMR (400 MHz, CD3OD), presumed to be a mixture of rotamers, characteristic signals: δ 7.23-7.30 (m, 4H), 7.15-7.22 (m, 1H), [4.68 (d, J=8.6 Hz) and 4.74 (d, J=8.0 Hz), total 1H], 3.39 and 3.40 (2 s, total 3H), 3.12 and 3.22 (2 br s, total 3H), [2.82 (d, J=6.0 Hz) and 2.84 (d, J=6.0 Hz), total 1H], 2.29 and 2.30 (2 s, total 3H), [1.27 (d, J=6.8 Hz) and 1.29 (d, J=6.6 Hz), total 3H], [0.84 (t, J=7.4 Hz) and 0.87 (t, J=7.4 Hz), total 3H].

Workup

  1. customwas purified by silica gel chromatography (Gradient: 0% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-21eb320f4d984758a70c1330056ae2ab
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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