Ninhydrin → HCID 23292698, compound

HRID 365652Notes

Reaction equation

HRID 365652 reaction equation
[CH3:1][Si:2]([CH3:16])([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=O.[CH:17]1[CH:18]=[CH:19][C:20]2N(O)N=N[C:21]=2[CH:22]=1.C1CCC([N:33]=C=NC2CCCCC2)CC1.[CH:42]1[CH:47]=[C:46]2C(C(O)(O)[C:51](=O)[C:45]2=[CH:44][CH:43]=1)=O>CN(C=O)C>[CH3:16][Si:2]([CH3:1])([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([NH:33][CH:51]([C:45]1[CH:46]=[CH:47][CH:42]=[CH:43][CH:44]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:22]=1)=[O:7]

Participants

6

Reactant 4

HCID 10236NinhydrinHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10537921HCID 10537921, compound

Product 1

HCID 23292698HCID 23292698, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To BHA resin (obtained from 7.0 g BHA resin hydrochloride after neutralization with 10% Et3N in CH2Cl2 and washing with CH2Cl2, 7.77 mmMol) was added a solution of the above 3-[dimethyl-4-(hydroxymethyl)phenylsilyl]propionic acid (2.36 g, 9.9 mmol) in DMF (30 mL). To this were added HOBt (2.7 g, 20 mmol) and DCC (2.1 g, 9.9 mmol). The reaction was shaken for 16 h, washed with DMF (2×30 mL), (1:1) CHCl3 :MeOH (2×30 mL), CH2Cl2 (2×30 mL), hexane (30 mL) and dried under vacuum for 24 h to give resin 2-Scheme 6. (8.66 g, 0.90 mmol/g): negative ninhydrin test; (Kaiser et al., Anal. Biochem. 1970, 34, 594-598). MAS 1H NMR (500 Mhz) δ 0.20 (6H, Si(CH3)2 's), 1.05 (2H, CH2CON), 2.10 (2H, SiCH2C), 2.80 (1H, HO), 4.52 (2H, OCH2 --Ar), 7.22, 7.40 (4H, ArH's).

Workup

  1. washwashed with DMF (2×30 mL), (1:1) CHCl3
  2. dry with materialMeOH (2×30 mL), CH2Cl2 (2×30 mL), hexane (30 mL) and dried under vacuum for 24 h
  3. customto give resin 2-Scheme 6

Sources & evidence

ORD record
ord-642a45b99f9a4530af6266058cc3ceb5
Source dataset
uspto-grants-2000_10
Patent number
US06127489

Reaction notes

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