1,2-Dichloroethane → HCID 131727149, compound

HRID 269622Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:14][C@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16](O)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([N:43]([CH2:47][CH2:48][NH2:49])[C:44](=[O:46])[OH:45])C1C=CC=CC=1.[CH:50](N(C(C)C)CC)(C)C.C(Cl)CCl.[CH:63]1[CH:64]=[CH:65][C:66]2N(O)N=N[C:67]=2[CH:68]=1>CN(C=O)C>[CH2:50]([O:45][C:44](=[O:46])[NH:43][CH2:47][CH2:48][NH:49][C:16](=[O:17])[C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:14][C@@H:13]([O:27][Si:28]([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:67]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:68]=1

Participants

Conditions

Temperature: 0 °C

Procedure

85 mg (0.17 mmol) of 5-benzyloxycarbonylamino-2 (S)-tert-butoxycarbonylamino-4 (R)-(tert-butyldimethylsilanyloxy)pentanoic acid (Example 14A), 67.1 mg (0.29 mmol) of benzyl-(2-aminoethyl)carbamate hydrochloride and 0.05 ml (0.29 mmol) of diisopropylethylamine are dissolved in 3 ml of DMF and cooled to 0° C. 55.8 mg (0.29 mmol) of EDC and 7.6 mg (0.06 mmol) of HOBT are added, and the mixture is allowed to warm to room temperature and is stirred overnight. The mixture is then concentrated in vacuo and purified by chromatography on silica gel (dichloromethane/methanol 20:1)

Workup

temperatureto warm to room temperature
concentrationThe mixture is then concentrated in vacuo
custompurified by chromatography on silica gel (dichloromethane/methanol 20:1)

Sources & evidence

ORD record: ord-13ad7057ce484320b6fb4e0fa1d2e47a
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446102B2

Reaction notes

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