2,6-Lutidine → (R)-tert-butyl 2-(2-(benzyloxycarbonylamino)-2-phenylacetamido)acetate

HRID 458928Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:19]([OH:21])=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:23][C@H:24]([C:29]([OH:31])=[O:30])C(C)(C)C.N1[C:37]([CH3:38])=[CH:36]C=CC=1C.[CH3:40]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:19](=[O:21])[NH:23][CH2:24][C:29]([O:31][C:37]([CH3:36])([CH3:38])[CH3:40])=[O:30])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(R)-N-Benzyloxycarbonyl-α-carboxybenzylamine (10 g, 35.0 mmol) and t-butylglycine hydrochloride (6.3 g, 37.4 mmol) was dissolved in DCM (200 ml) with 2,6-lutidine (8.2 ml, 70.4 mmol). After stirring 5 min at 0° C. TBTU (12.4 g, 38.6 mmol) was added and stirring was continued 1 hour 30 min at 0° C. and 3 hours 45 min at room temperature. The reaction mixture was washed with water (2×100 ml), dried (MgSO4) and purified with flash chromatography (DCM:EtOAc 7:1→5:1) to give the title compound (13 g, 94%). NMR (500 MHz) 1.45 (s, 9H), 3.84 (d, 1H), 4.00 (dd, 1H), 5.10 (m, 2H), 5.28 (brs, 1H), 6.13 (brs, 1H), 6.23 (brs, 1H), 7.30–7.44 (m, 10H).

Workup

stirringstirring
waitwas continued 1 hour 30 min at 0° C. and 3 hours 45 min at room temperature
washThe reaction mixture was washed with water (2×100 ml)
dry with materialdried (MgSO4)
custompurified with flash chromatography (DCM:EtOAc 7:1→5:1)

Sources & evidence

ORD record: ord-ef471c3bf54741148db44f16b9112137
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192945B2

Reaction notes

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