Triphenylphosphine → HCID 86707857, compound

HRID 922420Notes

Reaction equation

HRID 922420 reaction equation
[CH:1]1([N:4]([C@@H:20]([C:22]2[NH:31][C:30](=O)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH3:21])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.[CH3:33][O:34][CH2:35][CH2:36][CH2:37]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:1]1([N:4]([C@@H:20]([C:22]2[N:31]=[C:30]([CH2:37][CH2:36][CH2:35][O:34][CH3:33])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH3:21])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 741163-Methoxy-1-propanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136338086HCID 136338086, compound

Product 1

HCID 86707857HCID 86707857, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2R)-2-({cyclopropyl[(1R)-1-(4-oxo-3,4-dihydroquinazolin-2-yl)ethyl]amino}carbonyl)morpholin-4-carboxylate (88 mg), 3-methoxy-1-propanol (36 mg) and triphenylphosphine (105 mg) in tetrahydrofuran (4 mL) was added dropwise diisopropyl azodicarboxylate (84 μL) under ice-cooling, and the mixture was stirred at room temperature for 19 hours. The reaction solution was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/2) to give tert-butyl (2R)-2-[(cyclopropyl{(1R)-1-[4-(3-methoxypropyl)quinazolin-2-yl]ethyl}amino)carbonyl]morpholin-4-carboxylate [Ex(168-1)] (38 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/2)

Sources & evidence

ORD record
ord-2d5790a0ff7f4752a1598426aabaa501
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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