Ethyl isocyanate → HCID 69550224, compound

HRID 1582738Notes

Reaction equation

HRID 1582738 reaction equation
[CH:1]([CH:5]([N:34]([CH3:51])[C:35]([CH:37]([NH:41][C:42](=[O:50])[CH:43]([N:47]([CH3:49])[CH3:48])[CH:44]([CH3:46])[CH3:45])[CH:38]([CH3:40])[CH3:39])=[O:36])[CH:6]([O:32][CH3:33])[CH2:7][C:8]([N:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH:15]([S:30][CH3:31])[CH:16]([C:18](=[O:29])[NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=1)[CH3:17])=[O:9])([CH2:3][CH3:4])[CH3:2].[CH2:52]([N:54]=[C:55]=[O:56])[CH3:53].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:49][N:47]([CH3:48])[CH:43]([CH:44]([CH3:46])[CH3:45])[C:42]([NH:41][CH:37]([CH:38]([CH3:39])[CH3:40])[C:35]([N:34]([CH3:51])[CH:5]([CH:1]([CH3:2])[CH2:3][CH3:4])[CH:6]([O:32][CH3:33])[CH2:7][C:8]([N:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH:15]([S:30][CH3:31])[CH:16]([CH3:17])[C:18]([NH:19][CH2:20][CH2:21][C:22]1[CH:23]=[C:24]([O:28][C:55](=[O:56])[NH:54][CH2:52][CH3:53])[CH:25]=[CH:26][CH:27]=1)=[O:29])=[O:9])=[O:36])=[O:50]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 10234018HCID 10234018, compound

Product 1

HCID 69550224HCID 69550224, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(1-{[1-sec-butyl-4-(2-{2-[2-(3-hydroxy-phenyl)-ethylcarbamoyl]-1-methylsulfanyl-propyl}-pyrrolidin-1-yl)-2-methoxy-4-oxo-butyl]-methyl-carbamoyl}-2-methyl-propyl)-2-dimethylamino-3-methyl-butyramide (30 mg, 0.035 mmol) in CH2Cl2 (0.5 mL) were added ethyl isocyanate (0.042 mL, 0.53 mmol) and diisopropylethylamine (0.062 mL, 0.35 mmol) at room temperature. After being stirred at room temperature for 13hr, the mixture was concentrated in vacuo to give a crude oil (58 mg), which was purified by preparative HPLC (column:ODS-8OTs, eluent: 35/35 H2O:CH3CN/0.05% TFA). The appropriate fractions were lyophilized to give the title compound as a white amorphous powder (13 mg, 39%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a crude oil (58 mg), which
  3. customwas purified by preparative HPLC (column:ODS-8OTs, eluent: 35/35 H2O:CH3CN/0.05% TFA)

Sources & evidence

ORD record
ord-5ac4a5b6d1854aae989f29d763255330
Source dataset
uspto-grants-2004_05
Patent number
US06737409B2

Reaction notes

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