2,2-Diphenylacetyl chloride → HCID 86755897, compound

HRID 366031Notes

Reaction equation

HRID 366031 reaction equation
Cl.[C:2]([NH:12][CH2:13][CH2:14][CH2:15][C@H:16]([C:18]([NH:20][C@@H:21]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH3:22])=[O:19])[NH2:17])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(=O)(O)[O-].[Na+].[C:35]1([CH:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:42](Cl)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[C:2]([NH:12][CH2:13][CH2:14][CH2:15][C@H:16]([C:18]([NH:20][C@@H:21]([C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[CH3:22])=[O:19])[NH:17][C:42](=[O:43])[CH:41]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3]

Participants

5

Reactant 3

HCID 746372,2-Diphenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 86755898HCID 86755898, compound

Product 1

HCID 86755897HCID 86755897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-N5 -(Cbz)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide hydrochloride (28.1 g; 66.6 mmol; from step (c) above) was dissolved in THF (500 mL) and solid sodium bicarbonate (22.4 g; 266.4 mmol; 4 eq.) was slowly added. A solution of diphenylacetylchloride (21.4 g; 66.60 mmol) in THF was then slowly added dropwise over 30 minutes. The reaction was monitored by TLC analysis. After the reaction was judged complete, the solvent was removed under vacuum and the residue was dissolved in a mixture of THF, EtOAc and MeOH and washed with saturated aqueous sodium bicarbonate, water, saturated KHSO4 and brine. The organics were dried over Na2SO4, filtered and concentrated to dryness to yield 29.2 g (0.050 mol; 76%) of the sub-title compound.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in a mixture of THF, EtOAc and MeOH
  3. washwashed with saturated aqueous sodium bicarbonate, water, saturated KHSO4 and brine
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f87f05fee01146679bd9041e4faa8816
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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