Methanol → HCID 86585773, compound

HRID 1058308Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1C=[CH:16][C:15](Cl)=[CH:14][C:11]=1[CH2:12]N)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22](C(C)C)CC)(C)C.[Br:28][CH2:29][C:30](Br)=[O:31].CO.Cl[CH2:36][Cl:37]>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH:29]([Br:28])[C:30]([NH2:22])=[O:31])[C:11]1[CH:12]=[C:36]([Cl:37])[CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 5

HCID 887Methanol

HCID 6344Dichloromethane2×

HCID 61147Bromoacetyl bromide

HCID 81531Diisopropylethylamine

HCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

Product 1

HCID 86585773HCID 86585773, compound

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamine (0.52 g, 1.93 mmol) in dichloromethane (2 mL) was added diisopropylethylamine (0.34 mL, 1.95 mmol) and the solution was cooled to −78° C. Bromoacetyl bromide (0.19 mL, 2.12 mmol) was added slowly and after the addition was complete, the temperature was raised to 0° C. The reaction was complete in 15 min based on the disappearance of starting amine on silica gel TLC a 95:5 mixture of dichloromethane to methanol as mobile phase. The solvent was removed on a rotary evaporator to yield N-(2-(tert-butyloxycarbonylaminomethyl-5-chlorobenzyl)bromoacetamide (0.75 g).

Workup

additionafter the addition
temperaturethe temperature was raised to 0° C
customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record: ord-8f978613fe3b4555afc57afb00fc6b1c
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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