Isopropyl chloroformate → {3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-carbamic acid isopropyl ester

HRID 2171042Notes

Reaction equation

HRID 2171042 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:6][O:5][CH2:4]1.C(N(CC)CC)C.[C:36](Cl)(=[O:41])[O:37][CH:38]([CH3:40])[CH3:39].COC1C(OC)=CC=C(C2C=CC=C3C=2CCC3=O)C=1OCC1(CNC(=O)C)COC1>ClCCl>[CH:38]([O:37][C:36](=[O:41])[NH:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:10]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH2:22][C:23]4=[O:28])=[CH:11][CH:12]=[C:13]([O:17][CH3:18])[C:14]=2[O:15][CH3:16])[CH2:4][O:5][CH2:6]1)([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 54577376N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-acetamideHCID 674679514-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one2×

Product 1

HCID 67467758{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-carbamic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 191) (150 mg, 0.3916 mmol) in dichloromethane (15 mL), were added triethylamine (118 mg, 1.174 mmol) and isopropyl carbonochloridate (95 mg, 0.783 mmol) and the resultant reaction mixture was subjected to the conditions used in the preparation of Compound 192 to afford the title compound as a solid.

Workup

  1. customthe resultant reaction mixture

Sources & evidence

ORD record
ord-10fa4e10e5af4076b9dfac54873fcd79
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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