Diphosgene → (2S)-2-[1-Hydroxy-2-(4-methoxyphenoxy)ethyl]-l-[N-(4-methoxybenzylaminocarbonyl)-L-prolyl]pyrrolidine

HRID 1720503Notes

Reaction equation

HRID 1720503 reaction equation
ClC(OC(Cl)(Cl)Cl)=O.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.Cl.OC([C@@H]1CCCN1C(=O)[C@@H]1CCCN1)COC1C=CC(OC)=CC=1.C([O:48][C:49]([N:51]1[CH2:74][CH2:73][CH2:72][C@H:52]1[C:53]([N:55]1[CH2:59][CH2:58][CH2:57][C@H:56]1[CH:60]([OH:71])[CH2:61][O:62][C:63]1[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=1)=[O:54])=O)(C)(C)C.Cl.O1CCOCC1>C(N(CC)CC)C>[OH:71][CH:60]([C@@H:56]1[CH2:57][CH2:58][CH2:59][N:55]1[C:53](=[O:54])[C@@H:52]1[CH2:72][CH2:73][CH2:74][N:51]1[C:49]([NH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)=[O:48])[CH2:61][O:62][C:63]1[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=1

Participants

7

Reactant 5

HCID 10426DiphosgeneHCID 754524-MethoxybenzylamineHCID 204431481,4-Dioxane hydrochlorideHCID 22860058(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidineHCID 22860064(2S)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]-l-(L-prolyl)pyrrolidine hydrochloride

Product 1

HCID 22860066(2S)-2-[1-Hydroxy-2-(4-methoxyphenoxy)ethyl]-l-[N-(4-methoxybenzylaminocarbonyl)-L-prolyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

By the same procedure as in Example 24-A) using trichloromethyl chloroformate (0.20 ml), 4-methoxybenzylamine (449 mg), triethylamine (0.45 ml+0.89 ml) and (2S)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]-l-(L-prolyl)pyrrolidine hydrochloride (1.18 g) as obtained by treating (2S)-1-[N-(t-butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2-(4-methoxyphenoxy) ethyl]pyrrolidine obtained in Example 22-A) with 4N hydrochloric acid/1,4-dioxane, there was obtained 661 mg of the title compound.

Workup

  1. customas obtained

Sources & evidence

ORD record
ord-ac3048f02d4b47059dcb80ddaf248134
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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