tert-Butanol → HCID 18926523, compound

HRID 1600191Notes

Reaction equation

C([CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[C:9]([CH3:21])[N:10]2[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[C:53]([OH:57])([CH3:56])([CH3:55])[CH3:54]>>[C:53]([O:57][C:51]([NH:48][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[C:9]([CH3:21])[N:10]2[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:36])([CH3:56])([CH3:55])[CH3:54]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 18926566HCID 18926566, compound

Product 1

HCID 18926523HCID 18926523, compound

Procedure

Treatment of methyl 4-(2-carboxyethyl)-2-methyl-3-(3-pyridylmethyl)-1H-indole-1-propanoate (3.70 g) with diphenylphosphoryl azide (2.95 g), triethylamine (1.08 g), and t-butanol (30 ml) as described in Preparation 29 gave the title compound as an oil (3.46 g), Rf. 0.5 (SS2). δ(CDCl3): 1.44(9H,s), 2.37(3H,s), 2.77(2H,t), 2.87(2H,t), 3.23(2H,m), 3.68(3H,s), 4.28(2H,s), 4.45(2H,t), 4.53(1H,br), 6.82(1H,d), 7.10-7.13(2H,m), 7.21(1H,d), 7.29(1H,d), 8.38-8.42(2H,m).

Sources & evidence

ORD record: ord-d0f4dd005c3b4287b95842bd8d627606
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05744488

Reaction notes

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