Ethyl isocyanate → HCID 69818230, compound

HRID 2417428Notes

Reaction equation

HRID 2417428 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C@H:7]([N:10]([CH2:18][C@H:19]([OH:28])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)C(=O)OC(C)(C)C)[CH2:8][OH:9])=[CH:4][CH:3]=1.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32].[CH2:36](N(C(C)C)C(C)C)C.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].O>ClC(Cl)C.CN1CCCC1=O>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[OH:9][CH2:8][C@@H:7]([NH:10][CH2:18][C@H:19]([OH:28])[CH2:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:34]([NH:33][CH2:31][CH2:32][CH3:36])=[O:35])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 22392675Trifluoroacetic acid waterHCID 69817650HCID 69817650, compound

Product 1

HCID 69818230HCID 69818230, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

To a 0.5 M solution of tert-butyl N-[(1S)-1-(4-aminobenzyl)-2-hydroxyethyl]-N-((2S)-2-hydroxy-3-phenoxypropyl)carbamate in dichloroethane (40 μl) were added successively 2.0 M solution of N,O-bis(trimethylsilyl)-acetamide in 1-methyl-2-pyrrolidinone (10 μl), 1.0 M solution of ethyl isocyanate in 1-methyl-2-pyrrolidinone (24 μl), and 0.1 M solution of N-ethyldiisopropylamine in 1-methyl-2-pyrrolidinone (20 μl) at room temperature. After shaking at room temperature for 30 minutes, the solution was treated with 500 μl of trifluoroacetic acid/water (95/5) at 50° C. for 30 minutes. The mixture was evaporated and the residue was purified by reverse phase HPLC (0-100% acetonitrile in water (containing 0.1% trifluoroacetic acid)) to give N-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenyl]-N′-propylurea trifluoroacetate (5.51 mg) as a pale yellow oil.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by reverse phase HPLC (0-100% acetonitrile in water (containing 0.1% trifluoroacetic acid))

Sources & evidence

ORD record
ord-e210aa8857e04c219de35fe1e40ce5d5
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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