(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid → {(S)-1-[(S)-1-(2-Methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

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Reaction Steps

In a similar manner to that described for the preparation of {(S)-1-[(S)-1-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (Intermediate 12), (S)-3-amino-1-(2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate salt (Step 1 above) (460 mg) and Boc-N-Me-Ala-OH (223.3 mg, 1.1 mmol) were converted to the title compound (390 mg, 73.2%) obtained as a white solid. LC-MS: 533 (M+H).

Provenance & Evidence