Ammonia → HCID 54308607, compound

HRID 231938Notes

Reaction equation

HRID 231938 reaction equation
[CH:1]1([C:5]([NH:7][C@H:8]([C:24]([NH:26][CH:27]([P:35](=[O:40])([O:38]C)[O:36]C)[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[O:6])[CH2:4][CH2:3][CH2:2]1.C[Si](Br)(C)C.C(O)(C)C.N>ClCCl.O>[CH:1]1([C:5]([NH:7][C@H:8]([C:24]([NH:26][CH:27]([P:35](=[O:36])([OH:40])[OH:38])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3776IsopropanolHCID 76113BromotrimethylsilaneHCID 86743240HCID 86743240, compound

Product 1

HCID 54308607HCID 54308607, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The dimethyl ester product from part (e) (1.04 g., 1.81 mmole) is dissolved in dichloromethane (10 ml.) and treated with trimethysilylbromide (0.52 ml., 605 mg., 3.96 mmole). The mixture is stirred under argon overnight then concentrated in vacuo. Dioxane (15 ml.) and water (5 ml.) are added and the resulting mixture is stirred for 15 minutes and then concentrated. Residual water is chased three times with acetonitrile (20 ml.) giving 1.06 g. of [1-[[N2 -(cyclobutylcarbonyl)-N6 -[(phenylmethoxy)carbonyl]-L-lysyl]-2-phenylethyl]phosphonic acid as an organe-yellow foam. TLC (silica gel; isopropanol:ammonia:water, 7:2:1) Rf =0.42.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionDioxane (15 ml.) and water (5 ml.) are added
  3. stirringthe resulting mixture is stirred for 15 minutes
  4. concentrationconcentrated
  5. customgiving 1.06 g

Sources & evidence

ORD record
ord-3043322370f843d3956b08799b3953b3
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

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