Sodium Hydroxide → (R)-[4-(4-Benzyl-phenoxy)-phenyl]-tert-butoxycarbonylamino acetic acid

HRID 1669514Notes

Reaction equation

HRID 1669514 reaction equation
C[O:2][C:3](=[O:33])[C@@H:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+]>>[CH2:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][C:16]2[CH:17]=[CH:18][C:13]([C@@H:4]([NH:5][C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])[C:3]([OH:33])=[O:2])=[CH:14][CH:15]=2)=[CH:21][CH:22]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 67352764(R)-[4-(4-Benzyl-phenoxy)-phenyl]-tert-butoxycarbonylamino acetic acid methyl ester

Product 1

HCID 67351927(R)-[4-(4-Benzyl-phenoxy)-phenyl]-tert-butoxycarbonylamino acetic acidYield 99%

Procedure

The title compound was prepared from the product from step 2 (1.3 g, 2.2 mmol) and NaOH (0.2 g, 4.4 mmol) using the Step 7 procedure of example 1 with 99% yield (1.0 g). 1HNMR (CDCl3) δ 1.43 (s, 9H), 3.86 (s, 2H), 4.71 (br, 1H), 4.93 (br, 1H), 5.76 (br, 1H), 6.75 (m, 4H), 7.02 (d, J=6.8 Hz, 2H), 7.13 (m, 3H), 7.23 (m, 4H), MS m/z 432 (M−1).

Sources & evidence

ORD record
ord-8f94ff91679c4810af2386f41af675f2
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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