Monobasic potassium phosphate → 11-carboxyundecyl 5-(Boc-amino)-4-oxopentanoate

HRID 1771060Notes

Reaction equation

HRID 1771060 reaction equation
[C:1]([NH:8][CH2:9][C:10](=[O:35])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]CC(Cl)(Cl)Cl)=[O:28])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].OP([O-])(O)=O.[K+]>O1CCCC1.[Zn]>[C:1]([NH:8][CH2:9][C:10](=[O:35])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 1182071072,2,2-trichloroethyl 12-[5-(Boc-amino)-4-oxopentanoyloxy]dodecanoate

Product 1

HCID 9003450311-carboxyundecyl 5-(Boc-amino)-4-oxopentanoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared from the product of 14b (1.38 g; 2.5 mmol) in tetrahydrofuran (25 mL) following the procedure in Example 12c and using the same quantities of 1 M KH2PO4 solution and zinc powder. Following work-up, 1.0 g (93%) product was obtained (pale yellow oil).

Sources & evidence

ORD record
ord-fddf8714651c4ee88ec6496d3c1dae1f
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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