(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid → HCID 178454229, compound

HRID 2075773Notes

Reaction equation

HRID 2075773 reaction equation
[C:1]([O:5][C:6](=[O:47])[NH:7][C@H:8]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:9]([N:11]1[CH2:16][CH2:15]C[CH2:13][C@H:12]1[C:17](=[O:40])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][C:27]2[C:28]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[OH:39])=[N:29][NH:30][CH:31]=2)=[CH:21][CH:20]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].N(C(OC(C)(C)C)=O)[C@@H](C(O)=[O:57])C1C=CC=CC=1>>[C:1]([O:5][C:6](=[O:47])[NH:7][C@H:8]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:9]([N:11]1[CH2:16][CH2:15][O:57][CH2:13][C@H:12]1[C:17](=[O:40])[NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]#[C:26][C:27]2[C:28]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[OH:39])=[N:29][NH:30][CH:31]=2)=[CH:23][CH:24]=1)=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acidHCID 178454228HCID 178454228, compound

Product 1

HCID 178454229HCID 178454229, compound

Procedure

Using the same procedure for the preparation of 27A, reaction of compound 29A with BOC-D-Phg-OH (11A) afforded the title compound 30A, which was purified by silica column chromatography eluting with dichloromethane/ethyl acetate (10/1, 4/1, 3/1) to give pure 30A as a white powder in similar yield. 1H NMR (CDCl3, 500 MHz) δ 10.73 (br s, 1H), 8.75 (s, 1H), 8.63 (s, 1H), 7.91 (d, 2H, J=8.5 Hz), 7.84 (s, 1H), 7.58 (d, 2H, J=7.5 Hz), 7.44 (m, 5H), 7.21 (d, 1H, J=9.0 Hz), 6.98 (d, 1H, J=8.0 Hz), 5.48 (d, 1H, J=6.0 Hz), 5.40 (d, 1H, J=5.0 Hz), 5.30 (s, 1H), 4.83 (d, 1H, J=12.0 Hz), 3.79 (d, 1H, J=13□0 Hz), 3.66 (t, 1H, J=13.0 Hz), 3.60 (t, 1H, J=1.0 Hz), 3.44 (dd, 1H, J=11.0, 1.5 Hz), 3.08 (t, 1H, J=10.5 Hz), 1.45 (s, 9H). LCMS (ESI) m/z 678.24 (MNa+), 656.25 (MH+), 600.16, 556.17. HPLC: tR=5.12 min.

Sources & evidence

ORD record
ord-895c75c6b43d48ea98ca35b7db94b50d
Source dataset
uspto-grants-2011_04
Patent number
US07923004B2

Reaction notes

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