Isopropyl chloroformate → (+/-)-cis-3-Methyl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid isopropyl ester

HRID 1726463Notes

Reaction equation

[C:1]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20](Cl)(=[O:22])=[O:21])=[CH:12][CH:11]=1)(=[O:8])[C:2]1C=C[CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])C.ClC(O[CH:42]([CH3:44])[CH3:43])=O.N(C(C)C)=[C:46]=O>>[CH:24]([O:28][C:29]([N:31]1[CH2:32][CH2:33][C@H:34]([NH:37][S:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:44][C:42]=3[CH3:43])=[CH:11][CH:12]=2)(=[O:22])=[O:21])[C@H:35]([CH3:46])[CH2:36]1)=[O:30])([CH3:26])[CH3:27]

Participants

Reactant 4

HCID 7917Isopropyl chloroformate

HCID 61277Isopropyl isocyanate

HCID 12682914-Amino-1-Boc-piperidine

HCID 161057574-Benzoylamino-naphthalene-1-sulfonyl chloride

Product 1

HCID 10414442(+/-)-cis-3-Methyl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid isopropyl ester

Procedure

The title compounds were made following the general procedure in Scheme 5 and deprotection in Scheme 4-1, substituting 4-(2-methyl-benzoylamino)-naphthalene-1-sulfonyl chloride for 4-benzoylamino-naphthalene-1-sulfonyl chloride, (p)-4-amino-1-benzyl-3-methyl-piperidine for 4-amino-piperidine-1-carboxylic acid tert-butyl ester and isopropyl chloroformate for 2-isocyanato-propane. 1H NMR (300 MHz, CDCl3) δ 8.72 (d, 1H), 8.43 (d, 1H), 8.35 (d, 1H), 8.12 (d, 1H), 7.95 (d, 2H), 7.72 (m, 3H), 7.46 (m, 1H), 7.35(d, 2H), 4.85 (m, 1H), 4.66 (d, 1H), 3.55 (m, 1H), 3.37 (m, 1H), 3.17 (m, 2H), 2.59 (s, 3H), 1.74 (m, 1H), 1.58 (m, 1H), 1.40 (m, 2H) 1.18 (dd, 6H), 0.67 (m, 3H); LC/MS m/z 524 (M+H)+.

Sources & evidence

ORD record: ord-745d6d80796b49d6b5ef67c09eb61bb5
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491827B2

Reaction notes

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