1-Hydroxybenzotriazole → HCID 69211675, compound

HRID 2214271Notes

Reaction equation

HRID 2214271 reaction equation
[CH3:1][C:2]([O:5][C:6]([CH2:8][C@H:9]([NH2:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])[CH3:3].[C:18]([O:22][C:23](=[O:52])[CH2:24][CH:25]([CH2:29][CH2:30][CH2:31][S:32][C:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:26](O)=[O:27])([CH3:21])([CH3:20])[CH3:19].C1C=CC2N(O)N=NC=2C=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:13]([O:12][C:10](=[O:11])[CH:9]([NH:17][C:26](=[O:27])[CH:25]([CH2:24][C:23]([O:22][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:52])[CH2:29][CH2:30][CH2:31][S:32][C:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 7269469D-aspartic acid di-t-butyl esterHCID 69210030HCID 69210030, compound

Product 1

HCID 69211675HCID 69211675, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To H-Asp (OtBu)-OtBu hydrochloride salt (28 mg, 0.10 mmol) in dry DMF (2 mL) was sequentially added at room temperature 2-(3-tritylsulfanyl-propyl)-succinic acid 4-tert-butyl ester (50 mg, 0.10 mmol), HOBt (14 mg, 0.10 mmol), PYBOP (56 mg, 0.11 mmol) and DIPEA (37 μL, 0.20 mmol). The usual aqueous work up yielded the title compound (62 mg, 86%) as a colorless residue: 1H NMR (CDCl3, 400 MHz) δ 7.41–7.38 (m, 6H), 7.29–7.25 (m, 6H), 6.60–6.57 (m, 1H), 4.68–4.56 (m, 1H), 3.18–3.14 (m, 2H), 2.89–2.80 (m, 1H), 2.74–2.52 (m, 2H), 2.43–2.36 (m, 1H), 2.32–2.19 (m, 1H), 2.12–2.07 (m, 2H), 1.83–1.80 (m, 2H), 1.60–1.53 (m, 1H), 1.45–1.40 (m, 27H); 13C (DEPT) (CDCl3, 100 MHz) δ 129.4, 127.7, 126.4, 49.0, 48.7, 46.1, 42.5, 37.8, 37.6, 37.2, 31.6, 31.5, 29.6, 27.9, 27.8, 27.7, 26.3, 26.2, 26.0.

Sources & evidence

ORD record
ord-b03b130cd48b4c869986eb4d770b34c8
Source dataset
uspto-grants-2006_09
Patent number
US07105539B2

Reaction notes

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