Propionyl chloride → N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3R,4S)4-[(phenethyl-propionyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide

HRID 1158488Notes

Reaction equation

HRID 1158488 reaction equation
C(OC(=O)[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17]O)[CH2:15][N:14](CC2C=CC=CC=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])(C)(C)C.[N+](C1C=CC=CC=1S([NH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=O)=O)([O-])=O.[C:48](Cl)(=[O:51])[CH2:49][CH3:50].[CH3:53][O:54][CH2:55][CH2:56][CH2:57][O:58][C:59]1[CH:60]=[C:61]([CH:65]=[CH:66][C:67]=1[O:68][CH3:69])[C:62]([OH:64])=O>O.CC#N.CC#N.O>[CH:8]([N:7]([CH2:11][C@@H:12]1[C@H:16]([CH2:17][N:39]([CH2:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:48](=[O:51])[CH2:49][CH3:50])[CH2:15][NH:14][CH2:13]1)[C:62](=[O:64])[C:61]1[CH:65]=[CH:66][C:67]([O:68][CH3:69])=[C:59]([O:58][CH2:57][CH2:56][CH2:55][O:54][CH3:53])[CH:60]=1)([CH3:9])[CH3:10]

Participants

8

Reactant 4

HCID 62324Propionyl chlorideHCID 7795552-nitro-N-phenethylbenzenesulfonamideHCID 190395024-Methoxy-3-(3-methoxypropoxy)benzoic acidHCID 68616191((3S*,4R*)-1-Benzyl-4-hydroxymethyl-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester

Product 1

HCID 11851830N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3R,4S)4-[(phenethyl-propionyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound is prepared analogously as described in Example 361 using ((3S*,4R*)-1-benzyl-4-hydroxymethyl-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester and 2-nitro-N-phenethyl-benzenesulfonamide in step F, then propionyl chloride as the acylating agent in step H and 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid as acylating agent in step J. MS (LC-MS): 554.4 [M+H]+; tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.26 min.

Workup

  1. custom5.26 min.

Sources & evidence

ORD record
ord-17df73a270cb43fe80eb6b3e6a227574
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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