Water → ({[2-(6-Amino-indol-1-yl)-2-oxo-ethyl]-methyl-carbamoyl}-methyl)-methyl-carbamic acid tert-butyl ester

HRID 423739Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[N:7]([CH3:28])[CH2:8][C:9](=[O:27])[N:10]([CH3:26])[CH2:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=2)[CH:16]=[CH:15]1)=[O:13])([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl.CCN(C(C)C)C(C)C.O>C(O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:8][C:9](=[O:27])[N:10]([CH2:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=2)[CH:16]=[CH:15]1)=[O:13])[CH3:26])[CH3:28])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl-({methyl-[2-(6-nitro-indol-1-yl)-2-oxo-ethyl]-carbamoyl}-methyl)-carbamic acid tert-butyl ester (12.4 g, 30.6 mmol), SnCl2.2H2O (34.5 g, 153.2 mmol) and DIEA (74.8 mL, 429 mmol) in ethanol (112 mL) was heated to 70° C. for 3 h. Water and EtOAc were added and the mixture was filtered through a short plug of Celite. The organic layer was separated, dried over Na2SO4 and concentrated to yield ({[2-(6-Amino-indol-1-yl)-2-oxo-ethyl]-methyl-carbamoyl}-methyl)-methyl-carbamic acid tert-butyl ester (B-26) (11.4 g, quant.). HPLC ret. time 2.11 min, 10-99% CH3CN, 5 min run; ESI-MS 375.3 m/z (MH+).

Workup

filtrationthe mixture was filtered through a short plug of Celite
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-8f390b5d6a724bd099ef933ee907f6c7
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101767B2

Reaction notes

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