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

HRID 1158399Notes

Reaction equation

HRID 1158399 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].[CH3:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][C:29]=1[O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42].C(N(CC)CC)C.C(OC(C)(C)C)=O>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([CH3:27])=[C:29]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=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

6

Reactant 4

HCID 8471TriethylamineHCID 61207tert-Butyl FormateHCID 573555373-(3-Methoxypropoxy)-4-methylbenzoic acidHCID 131728361(3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131728365(3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({[4-methyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

From (3S,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (5 g, 12.9 mmol), 4-methyl-3-(3-methoxy-propoxy)-benzoic acid (4.06 g, 18.1 mmol), BOPCI (4.6 g, 18.1 mmol) and triethylamine (7.2 mL, 51.7 mmol). TLC, Rf (AcOEt)=0.7. MS (LC-MS): 493 [M+H-Boc]+.

Sources & evidence

ORD record
ord-db1f9d4b31574ba888de5de448fef75a
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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