1-Propanol → HCID 71285790, compound

HRID 536533Notes

Reaction equation

HRID 536533 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[C:16]([OH:26])[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1.[CH2:31](O)[CH2:32][CH3:33].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>C1COCC1>[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[C:16]([O:26][CH2:31][CH2:32][CH3:33])[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1

Participants

6

Reactant 4

HCID 10311-PropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178429272HCID 178429272, compound

Product 1

HCID 71285790HCID 71285790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 80 mg (0.20 mmol) of the compound from example 109, 13 mg (16 μl, 0.22 mmol) of n-propanol and 57 mg (0.22 mmol) of triphenyl phosphine were suspended in 0.8 ml THF, mixed for 10 min in the ultrasonic bath and finally 44 mg (43 μl, 0.22 mmol) of diisopropyl azodicarboxylate was added and it was stirred for 1 h at RT. The reaction mixture was purified by preparative HPLC (Reprosil C18, gradient of acetonitrile/0.01% aq. formic acid). Yield: 48 mg (55% of theor.)

Workup

  1. additionwas added
  2. customThe reaction mixture was purified by preparative HPLC (Reprosil C18, gradient of acetonitrile/0.01% aq. formic acid)

Sources & evidence

ORD record
ord-75f5f70297214e109d4ef9b65495c3fb
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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