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

HRID 2377657Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=O)=[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:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([NH:23][CH2:24][C:29]([O:31][C:37]([CH3:36])([CH3:38])[CH3:40])=[O:30])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(2R)-{[(benzyloxy)carbonyl]amino}(phenyl)acetic acid (Z-(R)-Phg-OH) (10 g, 35.0 mmol) and tert-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 minutes at 0° C. TBTU (12.4 g, 38.6 mmol) was added and stirring was continued 1 hours 30 minutes at 0° C. and 3 hours 45 minutes at room temperature. The reaction mixture was washed with water (2×100 ml), dried (magnesium sulphate) and purified with flash chromatography (DCM:EtOAc 7:1→5:1) to give the tide compound (13 g, 94%). NMR (500 MHz): 1.45 (s, 9 H), 3.84 (d, 1 H), 4.00 (dd, 1 H), 5.10 (m, 2 H), 5.28 (br s, 1 H), 6.13 (br s, 1 H), 6.23 (br s, 1 H), 7.30-7.44 (m, 10 H).

Workup

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

Sources & evidence

ORD record: ord-2c10eff7136a44f2a155f873cb052615
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470678B2

Reaction notes

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