Diethyl Ether → HCID 131722033, compound

HRID 366033Notes

Reaction equation

HRID 366033 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]([O:29][CH3:30])=[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(N([CH2:36][CH3:37])CC)C.C([O:40][CH2:41][CH3:42])C>C(Cl)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:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)[CH3:22])=[O:19])[NH:17][C:41](=[O:40])[CH:42]([C:37]1[CH:36]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=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 3283Diethyl EtherHCID 8471TriethylamineHCID 131722034HCID 131722034, compound

Product 1

HCID 131722033HCID 131722033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepared according to the method described in Example 1(d) above from (R)-N5 -(Cbz)-(S)-N-[1-(4-methoxyphenyl)ethyl]ornithine amide hydrochloride (13.3 g; 30.5 mmol; from step (b) above) 2-nitrophenyl diphenyl acetate (9.8 g; 30.5 mmol; see Example 1(c) above), triethylamine (4.6 g; 45.8 mmol) and CH2Cl2 (600 mL), 60 hours reaction time. The reaction mixture was submitted to aqueous work up, dried, filtered and concentrated to give the crude product as a solid. The product was dissolved in CH2Cl2 and concentrated until solids began to form. Diethyl ether was added to precipitate more solids. The solids were collected and dried to give the sub-title compound as a white solid (13.5 g).

Workup

  1. customPrepared
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product as a solid
  6. concentrationconcentrated until solids
  7. customto form
  8. customto precipitate more solids
  9. customThe solids were collected
  10. customdried

Sources & evidence

ORD record
ord-ed8481188ba745bb91a95ec9c01e1b66
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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