Morpholine → HCID 131732924, compound

HRID 2168839Notes

Reaction equation

HRID 2168839 reaction equation
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[C:24]1([CH2:34][C@@H:35]([C:37]([OH:39])=[O:38])[NH2:36])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.[NH2:40][C@H:41]([C:45]([O:47]CC=C)=[O:46])[CH:42]([CH3:44])[CH3:43].N1CCOCC1.[Sn]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[C:24]1([CH2:34][C@@H:35]([C:37]([OH:39])=[O:38])[NH2:36])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.[NH2:40][C@H:41]([C:45]([OH:47])=[O:46])[CH:42]([CH3:44])[CH3:43]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5352426Tin atomHCID 131732923HCID 131732923, compound

Product 1

HCID 131732924HCID 131732924, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Cbz-Asp(O-tBu)-3-(1-naphtyl)-L-alanine-Val-OAllyl (0.312 g, 0.47 mmol) was dissolved in THF (13 mL) and rotary evaporated to dryness, the sample was then redissolved in THF (13 mL) and vacuum aspirated (3*1 min of aspiration), followed by replacement of the atmosphere with Argon. Pd(PPh3)4 (0.060 g, 0.11 eq) was added in one shot, the flask was then evacued with Argon. Morpholine (0.267 mL, 4.42 eq) was added and the flask covered with a tin foil. The mixture was kept under stirring for 3 days under Argon. The sample was evaporated to dryness and the obtained residue was subjected to purification on C18 using a gradient of MeOH/solution of H2O at pH=3.5 (10 to 100%) to get 0.18 g of the desired compound.

Workup

  1. customrotary evaporated to dryness
  2. dissolutionthe sample was then redissolved in THF (13 mL)
  3. custom(3*1 min of aspiration)
  4. customThe sample was evaporated to dryness
  5. customthe obtained residue was subjected to purification on C18

Sources & evidence

ORD record
ord-5c6ad100069e4f2e8a2b90eaf4c46a93
Source dataset
uspto-grants-2015_06
Patent number
US09045524B2

Reaction notes

Loading…