Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)hexanedioate → (2S)-2-amino-5-(4-hydroxybenzyl)hexanedioic acid

HRID 591321Notes

Reaction equation

HRID 591321 reaction equation
C([O:5][C:6](=[O:34])[C@@H:7]([NH:26]C(OC(C)(C)C)=O)[CH2:8][CH2:9][CH:10]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:11]([O:13]C(C)(C)C)=[O:12])(C)(C)C>CCCCCC.CC(O)C>[NH2:26][C@@H:7]([CH2:8][CH2:9][CH:10]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[C:11]([OH:13])=[O:12])[C:6]([OH:34])=[O:5]

Participants

3

Reactant 1

HCID 70957101Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)hexanedioate

Product 1

HCID 70977373(2S)-2-amino-5-(4-hydroxybenzyl)hexanedioic acidYield 48%

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

1.56 g (3.25 mmol) (2S)-2-tert.-Butoxycarbonylamino-5-(4-hydroxy-benzyl)-hexanedioic acid di-tert.-butyl ester (Example 41b) were purified by chiral HPLC (Chiralpak AD-H 5 μm 250×300 mm; hexan/2-propanol; 40 mL7 min). Two isomers were isolated (isomer 1: 362 mg and isomer 2: 424 mg). 0.15 g (0.31 mmol) isomer 1 and 0.15 g (0.31 mmol) isomer 2 were individually deprotected according to the procedure described in Example 41c, yielding 42 mg (51%) (2S)-2-amino-5-(4-hydroxybenzyl)hexanedioic acid—Isomers C5-1 and 40 mg (48%) (2S)-2-amino-5-(4-hydroxybenzyl)hexanedioic acid—Isomers C5-2.

Workup

  1. customTwo isomers were isolated (isomer 1: 362 mg and isomer 2: 424 mg)

Sources & evidence

ORD record
ord-8a73836a45b4436bb643d7df5a715968
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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