Diisopropylethylamine → HCID 14365061, compound

HRID 2278812Notes

Reaction equation

[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([OH:15])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH2:23][C@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1.Cl.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>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([NH:23][C@H:24]([C:35]([O:37][CH3:38])=[O:36])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)=[O:15])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.0 g (3.22 mmol) Boc-D-Phe(4-NO2)—OH (Iris Biotech) and 0.84 g (3.22 mmol) H-Phe(4-NO2)—OMe.HCl (Aldrich) were suspended in 25 ml of DMF and stirred on the ice bath. After addition of 1.66 g (3.22 mmol) of PyBOP and 1.67 ml (9.66 mmol) of DIPEA (pH 7-8), the mixture was stirred at 0° C. for 2.5 h. The solvent was removed in vacuo and the yellow oil was taken up in 5% KHSO4 soln./EtOAc. The organic phase was washed 3× with 5% KHSO4 soln., 1× with sat. NaCl soln., 3× with sat. NaHCO3 soln. and 3× with sat. NaCl soln. The organic phase was dried with MgSO4, filtered, and the solvent was removed in vacuo.

Workup

customThe solvent was removed in vacuo
washThe organic phase was washed 3× with 5% KHSO4 soln
dry with materialThe organic phase was dried with MgSO4
filtrationfiltered
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-2396abf1cc104981b28f95521cc2fe2a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133194B2

Reaction notes

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