Acetonitrile → Ammonium hydroxide methanol

HRID 366039Notes

Reaction equation

HRID 366039 reaction equation
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([NH:34][C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=1)[CH3:36])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(OCC1C=CC=CC=1)=[O:2].C(#N)C.C(Cl)Cl.C[Si](I)(C)C>C(N(CC)CC)C>[CH3:1][OH:2].[OH-:2].[NH4+:11].[C:19]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([NH:16][C@@H:15]([C:32]([NH:34][C@@H:35]([C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)[CH3:36])=[O:33])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 85247Trimethylsilyl iodide2×HCID 131722039HCID 131722039, compound

Product 2

HCID 21894508Ammonium hydroxide methanolHCID 86755912HCID 86755912, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Prepared according to the method described in Example 6(d) above from (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(R)-N-[1-(4-bromophenyl)ethyl]ornithine amide (1.00 g; 1.56 mmol; from step (c) above), acetonitrile (30 mL), CH2Cl2 (10 mL) and trimethylsilyl iodide (0.34 g, 1.70 mmol), 1.5 hours reaction time, followed by additional trimethylsilyl iodide (0.14 g; 0.70 mmol), 0.5 hours reaction time. Work up using triethylamine (10 mL) gave the crude product as an oil (1.00 g). The product was chromatographed on silica gel eluting with MeOH, then with MeOH:ammonium hydroxide (30:1) to give pure sub-title compound (free base) as an off-white crushable foam (0.57 g).

Workup

  1. customPrepared
  2. customgave the crude product as an oil (1.00 g)
  3. customThe product was chromatographed on silica gel eluting with MeOH

Sources & evidence

ORD record
ord-909aac45405c46eca8d10f07732b83b3
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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