Lithium Hydroxide → N-Boc-Tyr(Bn)-Ala-OH

HRID 2074349Notes

Reaction equation

HRID 2074349 reaction equation
[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:2]([C:18]([NH:20][C@H:21]([C:23]([O:25]C)=[O:24])[CH3:22])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1>[NH:1]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C@H:2]([C:18]([NH:20][C@H:21]([C:23]([OH:25])=[O:24])[CH3:22])=[O:19])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11178570N-Boc-Tyr(Bn)-Ala-OMe

Product 1

HCID 57611766N-Boc-Tyr(Bn)-Ala-OH

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Same procedure as above with N-Boc-Tyr(Bn)-Ala-OMe (1.55 g, 3.39 mmol), aqueous LiOH (1 M, 4 mL, 4 mmol) in THF (4 mL). A white solid was obtained (1.25 g, 83%) which was used in the next step without further purification. 1H NMR (200 MHz, CDCl3) δ 1.41 (s large, 12H, CH3, (CH3)3), 3.01 (m, 2H, CH2), 4.38 (m, 1H, CHα), 4.53 (m, 1H, CHα), 5.04 (s, 2H, CH2 (Bn)), 5.16 (broad s, 1H, NHBoc), 6.68 (m, 1H, NH amide), 6.91 (d, J=8.6 Hz, 2 aromatic H), 7.12 (d, J=8.6 Hz, 2 aromatic H), 7.33-7.44 (m, 5 aromatic H). 13C NMR (75 MHz, CDCl3) δ 18 (CH3), 28.2 ((CH3)3), 37.5 (CH2 Tyr), 48.2 (CHα Ala), 55.6 (CHα Tyr), 70 (CH2 (Bn)), 80.5 (C(CH3)3), 115, 127.4, 128, 128.5, 128.6, 130.4, 137 (11 aromatic C), 155.8, 157.8 (Car-O, CO carbamate), 171.6, 175.5 (CO acid, CO amide).

Workup

  1. customA white solid was obtained (1.25 g, 83%) which
  2. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c5c4c5812d40453f8640904b50b6a50a
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

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