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

HRID 356757Notes

Reaction equation

HRID 356757 reaction equation
N[C@@H](C)C(N[C@@H](C)C(N(CC)C[C@H](C)CO[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[CH2:22][C@@:21]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:24]([O:26]C)=[O:25])[CH2:20][CH2:19]2)=O)=O.[OH-].[Li+]>O1CCCC1.CO.O>[C:32]([O:31][C:29]([NH:28][C:21]1([C:24]([OH:26])=[O:25])[CH2:20][CH2:19][C:18]2[C:23](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:22]1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86753338HCID 86753338, compound

Product 1

HCID 27331772-[(tert-Butoxycarbonyl)amino]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

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).

Workup

  1. custompurification

Sources & evidence

ORD record
ord-74c2ef90beca48e1b45600c7ad1f8bff
Source dataset
uspto-grants-1998_11
Patent number
US05837807

Reaction notes

Loading…