Triphenylphosphine → HCID 66849850, compound

HRID 1678284Notes

Reaction equation

HRID 1678284 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:25][OH:26])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:47]([O:54][C:55](=[O:68])[NH:56][CH2:57][CH2:58][CH2:59][CH2:60][C:61]1[CH:66]=[CH:65][C:64](O)=[CH:63][CH:62]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:5][C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:25][O:26][C:64]1[CH:63]=[CH:62][C:61]([CH2:60][CH2:59][CH2:58][CH2:57][NH:56][C:55]([O:54][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:68])=[CH:66][CH:65]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 7128367N-(Triphenylmethyl)-L-serine methyl esterHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamine

Product 1

HCID 66849850HCID 66849850, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Commercially available N-trityl-L-serine methyl ester (1.60 g, 5.34 mmol) was combined with triphenylphosphine (1.28 g, 4.88 mmol) and [4-(4-hydroxyphenyl)butyl]carbamic acid benzyl ester (2.0 g, 6.68 mmol) in benzene (40 mL) at room temperature. Diisopropyl azodicarboxylate (0.958 mL, 4.86 mmol) was added dropwise and the reaction was stirred for 14 days. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, eluent: 6:1, v/v dichloromethane/ethyl acetate) to provide compound 10 (2.22 g, 51%). 1H NMR (300 MHz, CDCl3) δ 7.52 (m, 6H), 7.39-7.14 (m, 14H), 7.06 (d, 2H), 6.79 (d, 2H), 5.09 (s, 2H), 4.72 (m, 1H), 4.24 (m, 1H), 4.01 (m, 1H), 3.72 (m, 1H), 3.22 (s, 3H), 3.18 (m, 2H), 2.88 (d, 1H), 2.57 (m, 2H), 1.66-1.48 (m, 4H). Rf=0.91 (5:1 v/v dichloromethane/ethyl acetate).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, eluent: 6:1, v/v dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-53d4b5e1e762410da925771d984c93f0
Source dataset
uspto-grants-2011_08
Patent number
US08008494B2

Reaction notes

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