1,2-Dichloroethane → HCID 86585259, compound

HRID 1018286Notes

Reaction equation

HRID 1018286 reaction equation
C([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([I:18])[CH:12]=1)(OC(C)(C)C)=O.[C:22](OC(=O)C)(=[O:24])C.[CH2:29](Cl)[CH2:30]Cl.C1C=CC2N([OH:42])N=NC=2C=1.[NH3:43].C(O)(=O)[CH2:45][C:46]([CH2:51]C(O)=O)([C:48](O)=O)[OH:47]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.CC(O)C>[C:22]([NH:43][C:19](=[O:21])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:29](=[O:42])[CH3:30])=[C:13]([I:18])[CH:12]=1)[NH2:8])([O:47][C:46]([CH3:45])([CH3:48])[CH3:51])=[O:24]

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 311Citric AcidHCID 7918Acetic AnhydrideHCID 757711-HydroxybenzotriazoleHCID 15545208N-(tert-Butoxycarbonyl)-3-iodo-L-tyrosine

Product 1

HCID 86585259HCID 86585259, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of N-Boc-3-iodotyrosine (0.380 g, 0.93 mmol) in pyridine (1 mL) were added acetic anhydride (105 μL, 1.1 mmol) and DMAP (10 mg, cat). The solution was stirred 1.5 h then diluted in 5% citric acid (20 mL), and the product extracted with EtOAc. The organic solution was evaporated and the residue dissolved in MeCN (4 mL). To the stirred cold (ice bath) solution were added EDC (0.196 g, 1.0 mmol) and HOBt (0.135 g, 1.0 mmol). After stirring for 1 h, a 2 N solution of ammonia in iPrOH (3 mL) was added. The suspension was stirred 1 h at 5° C., the solid was filtered, the filtrate evaporated and the residue purified by flash chromatography (gradient 3-5% MeOH/chloroform) to yield N-Boc-O-acety-3-iodotyrosine amide.

Workup

  1. extractionthe product extracted with EtOAc
  2. customThe organic solution was evaporated
  3. dissolutionthe residue dissolved in MeCN (4 mL)
  4. stirringAfter stirring for 1 h
  5. stirringThe suspension was stirred 1 h at 5° C.
  6. filtrationthe solid was filtered
  7. customthe filtrate evaporated
  8. customthe residue purified by flash chromatography (gradient 3-5% MeOH/chloroform)

Sources & evidence

ORD record
ord-50bac30a98c64f61a0a82db87e51a682
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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