Ethyl chloroformate → HCID 178473665, compound

HRID 718634Notes

Reaction equation

HRID 718634 reaction equation
[OH:1][NH:2][C:3](=[NH:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]3[N:15]=[CH:16][CH:17]=[C:18]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:13]3=[N:12][C:11]=2[C:25]#[C:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)=[CH:6][N:5]=1.CCN(C(C)C)C(C)C.[C:47](Cl)(=[O:51])[O:48][CH2:49][CH3:50]>C1COCC1>[CH2:49]([O:48][C:47]([O:1][NH:2][C:3](=[NH:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]3[N:15]=[CH:16][CH:17]=[C:18]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[C:13]3=[N:12][C:11]=2[C:25]#[C:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)=[CH:6][N:5]=1)=[O:51])[CH3:50]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178513260HCID 178513260, compound

Product 1

HCID 178473665HCID 178473665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 42a (0.16 g, 0.33 mmol), DIEA (0.17 g, 1.3 mmol) and ethyl carbonochloridate (0.10 g, 0.93 mmol) in THF (10 mL), was stirred at rt for 2 h. The reaction was then quenched with water (50 mL). The solids formed were collected by filtration and washed with Et2O (2×30 mL) to obtain compound 42b as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H26N8O4: 563.2 (M+H). Found 563.2.

Workup

  1. customThe reaction was then quenched with water (50 mL)
  2. customThe solids formed
  3. filtrationwere collected by filtration
  4. washwashed with Et2O (2×30 mL)

Sources & evidence

ORD record
ord-65ed59ffbccc4b9eb2e339579d42870d
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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