Water → 2-(tert-Butyl-dimethyl-silanyloxy)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

HRID 1098088Notes

Reaction equation

HRID 1098088 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CC=CC=1.[C:15]([NH:32][CH2:33][CH:34]([C:36]([OH:38])=[O:37])[OH:35])([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16].O>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:2]([Si:5]([CH3:7])([CH3:6])[O:35][CH:34]([CH2:33][NH:32][C:15]([O:17][CH2:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C:36]([OH:38])=[O:37])([CH3:4])([CH3:3])[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 152225833-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-hydroxypropanoic acid

Product 1

HCID 586877542-(tert-Butyl-dimethyl-silanyloxy)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acidYield 96.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

TBDMSCl (1.01 g, 6.72 mmol), DMAP (0.19 g, 1.52 mmol) and pyridine (0.97 g, 12.2 mmol) were added to a stirred solution of FMOC-isoserine (1.00 g, 3.05 mmol) in DMF (20 mL). The reaction mixture was heated at 50° C. for 18 hrs. Water (10 mL) was added and the reaction mixture was concentrated in vacuo. DCM and HCl (0.5 M) were added and the two phases were separated. The aqueous phase was extracted two times with DCM. The organic extracts were combined concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with a gradient consisting of 20-100% EtOAc in heptane) to give the title compound (1.3 g). 1H NMR (500 MHz, CDCl3) δ 7.76 (d, 2H), 7.59 (m, 2H), 7.40 (t, 2H), 7.30 (m, 2H), 5.14 (br s, 1H), 4.29 (m, 4H), 3.53 (m, 2H), 0.91 (s, 9H), 0.10 (s, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionDCM and HCl (0.5 M) were added
  3. customthe two phases were separated
  4. extractionThe aqueous phase was extracted two times with DCM
  5. concentrationThe organic extracts were combined concentrated in vacuo
  6. customThe residue was purified with column chromatography (silica gel
  7. washeluting with a gradient

Sources & evidence

ORD record
ord-c5eeb2f8728d40938a03926b90435a6d
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…