Triphenylphosphine → methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl){[(9H-fluoren-9-ylmethoxy)carbonyl]-amino}ethanoate

HRID 2414609Notes

Reaction equation

HRID 2414609 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].[CH:31]1[C:43]2[CH:42]([CH2:44][O:45][C:46]([NH:48][C@H:49]([C:54]3[CH:59]=[CH:58][C:57](O)=[CH:56][CH:55]=3)[C:50]([O:52][CH3:53])=[O:51])=[O:47])[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35]=2[CH:34]=[CH:33][CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][O:20][C:57]1[CH:58]=[CH:59][C:54]([C@@H:49]([NH:48][C:46]([O:45][CH2:44][CH:42]2[C:43]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=3[C:36]3[C:41]2=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:47])[C:50]([O:52][CH3:53])=[O:51])=[CH:55][CH:56]=1)=[O:30])([CH3:27])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 86590203methyl (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-(4-hydroxyphenyl)acetate

Product 1

HCID 86587124methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl){[(9H-fluoren-9-ylmethoxy)carbonyl]-amino}ethanoateYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.465 g (1.77 mmol) of triphenylphosphine in 10 mL of THF was added 0.286 g (1.77 mmol) of tert-butyl N-(2-hydroxyethyl)-carbamate followed by 0.476 g (1.18 mmol) of methyl (2R)-{[(9H-fluoren-9-ylmethoxy)carbonyl]-amino}(4-hydroxyphenyl)ethanoate and 0.279 mL (1.77 mmol) of diethyl azodicarboxylate. The reaction was stirred overnight at room temperature and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to give 0.383 g of methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl){[(9H-fluoren-9-ylmethoxy)carbonyl]-amino}ethanoate as a white solid. Electrospray Mass Spec 547.2 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-c274d70c47c54b60ae3ac5f032bc7969
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

Loading…