Triethylamine → HCID 57052419, compound

HRID 1583950Notes

Reaction equation

HRID 1583950 reaction equation
[CH2:1]([O:3][P:4]([CH2:26][C:27](O)=[O:28])([CH2:6][CH:7]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[NH:49]1[CH2:60][CH2:59][CH2:58][C@H:50]1[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][P:4]([CH2:26][C:27]([N:49]1[CH2:60][CH2:59][CH2:58][C@H:50]1[C:51]([O:53][C:54]([CH3:56])([CH3:57])[CH3:55])=[O:52])=[O:28])([CH2:6][CH:7]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 20156115HCID 20156115, compound

Product 1

HCID 57052419HCID 57052419, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mono ester product from part (e) (0.81 g., 1.94 mmole) in tetrahydrofuran (4 ml.) at 0° in an argon atmosphere was treated with carbonyldiimidazole (0.31 g., 1.0 eq.). After one hour, triethylamine (0.3 ml., 1.1 eq.) then L-proline, t-butyl ester (0.43 g., 1.3 eq.) were added to the above mixture. After stirring at room temperature for 16 hours, the reaction mixture was diluted with ethyl acetate and then washed with water, 5% sodium bicarbonate, 5% potassium bisulfate (twice), brine, dried (MgSO4), and evaporated to give 0.9 g of 1-[[ethoxy[3-phenyl-2-[[(phenylmethoxy)carbonyl]amino]propyl]phosphinyl]acetyl]-L-proline, 1,1-dimethylethyl ester as a foam. Tlc (dichloromethane/acetic acid/methanol; 100/5/5) major spot at Rf =0.5.

Workup

  1. washwashed with water, 5% sodium bicarbonate, 5% potassium bisulfate (twice), brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-74eda7226a2f4ee5bd96b4be678d0880
Source dataset
uspto-grants-1985_11
Patent number
US04555506

Reaction notes

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