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

HRID 2074351Notes

Reaction equation

HRID 2074351 reaction equation
[NH:1]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([O:28]C)=[O:27])[CH2:22][C:23](=[O:25])[NH2:24])=[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:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][C:23](=[O:25])[NH2:24])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11249045N-Boc-Tyr(Bn)-Asn-OMe

Product 1

HCID 57611773N-Boc-Tyr(Bn)-Asn-OH

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Same procedure as above with N-Boc-Tyr(Bn)-Asn-OMe (1.035 g, 2.072 mmol), aqueous LiOH (1 M, 2.2 mL, 2.2 mmol) in THF (15 mL). A beige solid was obtained (1.03 g, 100%) which was used in the next step without further purification. 1H NMR (300 MHz, CD3OD) δ 1.35 (s, 9H, (CH3)3), 2.73-3.13 (m, 4H, CH2), 4.29 (m, 1H, CHα), 4.72 (m, 1H, CHα), 5.06 (s, 2H, CH2 (Bn)), 6.92 (d, J=5 Hz, 2 aromatic H), 7.17 (d, J=5 Hz, 2 aromatic H), 7.33-7.44 (m, 5 aromatic H). 13C NMR (75 MHz, CD3OD) δ 28.7 ((CH3)3), 37.7, 38.3 (CH2 Tyr and Asn), 50.4 (CHα Asn), 57.5 (CHα Tyr), 71 (CH2 (Bn)), 80.7 (C(CH3)3), 116.0, 128.5, 128.8, 129.5, 130.9, 131.5, 131.8, 138.8 (11 aromatic C), 157.6, 159.2 (Car-O, CO carbamate), 174.2, 174.4, 175.0 (CO acid, CO amide).

Workup

  1. customA beige solid was obtained (1.03 g, 100%) which
  2. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-dee1105ba9da4893b468ae8dea3d3dd0
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

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