Triethylamine → (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158389Notes

Reaction equation

HRID 1158389 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])[C@H:10]([C:18]([CH3:26])([CH3:25])[O:19][SiH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][C:30]=1[O:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[CH3:28].C(N(CC)CC)C.C(OC(C)(C)C)=O>O.CC#N.CC#N.O.C(Cl)Cl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([CH2:27][CH3:28])=[C:30]([O:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[CH:31]=2)[CH:15]([CH3:16])[CH3:17])[C@H:10]([C:18]([CH3:26])([CH3:25])[O:19][SiH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 61207tert-Butyl FormateHCID 573555384-Ethyl-3-(3-methoxypropoxy)benzoic acidHCID 131728361(3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131728364(3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 18373917Acetonitrile--water (1/1)SolventHCID 21226129Dichloromethane methanolSolvent

Procedure

From (3S,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (8.5 g, 22 mmol), 4-ethyl-3-(3-methoxy-propoxy)-benzoic acid (5.76 g, 24.2 mmol), BOPCI (6.16 g, 24.2 mmol) and triethylamine (12.3 g, 88 mmol). TLC, Rf (CH2Cl2/MeOH 95:5)=0.32. tR (HPLC, Macherey-Nagel 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): 8.81 min. MS (LC-MS): [M+H-BOC]+507.3

Workup

  1. custom8.81 min

Sources & evidence

ORD record
ord-e7ca5b31cb0f48a09f5577b7148ddd58
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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