4-Methylmorpholine → Benzyl [[[4-[(t-butoxycarbonyl)methoxy]piperidinyl]carbonyl]methyl]carbamate

HRID 1077909Notes

Reaction equation

HRID 1077909 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])=[CH:3][CH:2]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([O:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17]1.CN1CCOCC1>ClCCl>[C:27]([O:26][C:24]([CH2:23][O:22][CH:19]1[CH2:18][CH2:17][N:16]([C:13]([CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:7][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[O:15])[CH2:21][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetate

Product 1

HCID 10341285Benzyl [[[4-[(t-butoxycarbonyl)methoxy]piperidinyl]carbonyl]methyl]carbamateYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.8 g of Z-glycine are first activated with 5.4 g of CDMT and then coupled with 6.0 g of t-butyl 4-piperidinyloxyacetate and 6.3 ml of N-methylmorpholine in dichloromethane there are obtained 10 g of benzyl [[[4-[(t-butoxycarbonyl)methoxy]piperidinyl]carbonyl]methyl]carbamate. MS (EI): 406 (M+).

Sources & evidence

ORD record
ord-7bcade2f077144b09d10bf0f47181b14
Source dataset
uspto-grants-1996_08
Patent number
US05545658

Reaction notes

Loading…