Cyclobutanecarbonyl chloride → HCID 57870312, compound

HRID 1698372Notes

Reaction equation

HRID 1698372 reaction equation
C1C2C(COC([N:18]3[CH2:23][C@H:22]([C:24](=[O:44])[N:25]([CH:41]4[CH2:43][CH2:42]4)[CH2:26][C:27]4[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:28]=4)[CH2:21][C@H:20]([NH:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.[CH:53]1([C:57](Cl)=[O:58])[CH2:56][CH2:55][CH2:54]1>CC#N>[CH:41]1([N:25]([CH2:26][C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:28]=2)[C:24]([C@@H:22]2[CH2:21][C@H:20]([N:45]([CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:57]([CH:53]3[CH2:56][CH2:55][CH2:54]3)=[O:58])[CH2:19][NH:18][CH2:23]2)=[O:44])[CH2:43][CH2:42]1

Participants

4

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 67273412(3S,5R)-3-Benzylamino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 57870312HCID 57870312, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

The title compound is prepared analogously as described in Example 134 using (3S,5R)-3-Benzylamino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester and cyclobutanecarbonylchloride. MS: 557 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 3.34 min.

Workup

  1. custom3.34 min.

Sources & evidence

ORD record
ord-ffb67e7001054c36ba0f93d0ee5780ba
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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