Lithium Hydroxide → 2-[(tert-Butoxycarbonyl)amino]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

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Reaction Steps

In analogy to Example 4.3.8.a, 18.0 mg (32.0 mmol) of methyl (R)-8-[(S)-3-[[(S)-2-[(S)-2-amino-propionylamino]-propionyl]-ethyl-amino]-2-methyl-propoxy]-2-tert.butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate in 1 ml of tetrahydrofuran/methanol/water (3:1:1) were reacted with 320 μl of 1N lithium hydroxide solution. After working up and purification according to Example 4.3.8.a 17.0 mg (96.8%) of (R)-8-[(S)-3-[(S)-2-[(S)-2-amino-propionylamino]-propionyl]-ethyl-amino]-2-methyl-propoxy!-2-tert.butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid were obtained as a white powder. MS: 549 (M+H+), 216.9 (100), 91.1 (75), 149.0 (36), 513 (35), 471 (31), 109 (29).

Provenance & Evidence