HCID 71268079, compound → HCID 71259041, compound

HRID 526325Notes

Reaction equation

HRID 526325 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:15]([NH:28][C:29]([C@@H:31]2[CH2:36][CH2:35][CH2:34][N:33]([C:37](=[O:53])[CH2:38][CH2:39][CH:40]3[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][CH2:41]3)[CH2:32]2)=[O:30])[CH:16]([C:24]([O:26]C)=[O:25])[C:17]([O:19][C:20](C)(C)C)=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:15]([NH:28][C:29]([C@@H:31]2[CH2:36][CH2:35][CH2:34][N:33]([C:37](=[O:53])[CH2:38][CH2:39][CH:40]3[CH2:41][CH2:42][NH:43][CH2:44][CH2:45]3)[CH2:32]2)=[O:30])[CH:16]([C:17]([O:19][CH3:20])=[O:18])[C:24]([OH:26])=[O:25])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 71268079HCID 71268079, compound

Product 1

HCID 71259041HCID 71259041, compoundYield 116,215.797%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Tert-butyl methyl 2-[(S)-[3-(benzyloxy)phenyl]({[(3R)-1-{3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoyl}piperidin-3-yl]carbonyl}amino)methyl]propanedioate (700 mg, 0.95 mmol) was solved in formic acid (5.4 mL) and stored for 5 days at room temperature. The mixture was concentrated under reduced pressure to yield 640 g of raw (3S)-3-[3-(benzyloxy)phenyl]-2-(methoxycarbonyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid. The methyl ester in THF (65 mL) and triethylamine (2.5 mL, 18 mmol) was heated to 60° C. for 4 hours. After concentration under reduced pressure the residue was purified by preparative HPLC to yield 147 mg of methyl (3S)-3-[3-(benzyloxy)phenyl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoate.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-989b2a30ab524a1cb4a46e02e3702fae
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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