Benzyloxycarbonylglycine → HCID 66654564, compound

HRID 2036246Notes

Reaction equation

HRID 2036246 reaction equation
[C:1]([NH:11][CH2:12][C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[CH2:17]([O:19][C:20](=[O:40])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][NH:31]1)[CH3:18].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH2:17]([O:19][C:20](=[O:40])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][N:31]1[C:13](=[O:15])[CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH3:18]

Participants

7

Reactant 3

HCID 14349BenzyloxycarbonylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66654555HCID 66654555, compound

Product 1

HCID 66654564HCID 66654564, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-carbobenzyloxyglycine (1.07 g, 5.00 mmol, 1.0 eq.) and (±)-[4-fluoro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl ester hydrochloride (1.93 g, 5.00 mmol, 1.0 eq.) in DMF (30 mL) was treated with 4-(dimethylamino)pyridine (2.44 g, 20.00 mmol, 4.0 eq.) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.44 g, 7.50 mmol, 1.5 eq.) and the resulting solution was stirred at r.t. for 18 hours. The reaction mixture was diluted with AcOEt (500 mL). The diluted solution was washed with 1N aq. HCl soln. (3×200 mL), sat. aq. NaHCO3 soln. (3×200 mL), sat. aq. NaCl soln. (1×200 mL), dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash master (column: 100 g, flow: 35 mL/min, heptane to heptane+AcOEt) to yield the title product as a white foam.

Workup

  1. washThe diluted solution was washed with 1N aq. HCl soln
  2. dry with material(1×200 mL), dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash master (column: 100 g, flow: 35 mL/min, heptane to heptane+AcOEt)

Sources & evidence

ORD record
ord-cf3d6bb6ab224891a0214985c3fa6816
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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